Rupe Rearrgment
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The document discusses the Meyer-Schuster rearrangement and Rupe rearrangement, which are acid-catalyzed rearrangements of propargylic alcohols. The Meyer-Schuster rearrangement involves a [1,3]-shift of the hydroxyl group to form α,β-unsaturated aldehydes or ketones. The Rupe rearrangement is similar but involves a [1,2]-shift to form α,β-unsaturated ketones. Both reactions can be catalyzed by protic or Lewis acids. The products differ depending on whether the alkyne is terminal or disubstituted.
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![In 1922, K.H. Meyer and K. Schuster reported that the attempted
conversion of 1,1,3-triphenyl-2-propynol to the corresponding ethyl
ether with concentrated sulfuric acid and ethanol afforded 1,3,3-
triphenyl propenone, an α,β- unsaturated ketone.
The authors showed that the use of other reagents such as acetic
anhydride and acetyl chloride also brought about the same reaction.
A few years later, H. Rupe and co-workers investigated the acid-
catalyzed
rearrangement of a large number of α-acetylenic (propargylic)
alcohols. The acid-catalyzed isomerization of secondary and tertiary
propargylic alcohols, via a [1,3]-shift of the hydroxyl group, to the
corresponding α,β- unsaturated aldehydes or ketones is known as the
Meyer-Schuster rearrangement.](data:image/gif;base64,R0lGODlhAQABAIAAAAAAAP///yH5BAEAAAAALAAAAAABAAEAAAIBRAA7)
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The document summarizes the dienone-phenol rearrangement, which is the acid- or base-catalyzed migration of alkyl groups in cyclohexadienones, resulting in highly substituted phenols. It was first described in 1893 for the rearrangement of santonin to desmotroposantonin under acidic conditions, but was more fully characterized in 1930. The rearrangement requires only moderately strong acids and is exothermic. It proceeds by a [1,3] sigmatropic migration of C-C bonds, which actually occurs through two subsequent [1,2] alkyl shifts. Depending on the migrating group, other rearrangements such as [1,2], [1,3], [
Substrate Inhibition in Ruthenium(III) Catalyzed Oxidation of Propane-1,3-dio...
Substrate Inhibition in Ruthenium(III) Catalyzed Oxidation of Propane-1,3-dio...Ratnakaram Venkata Nadh
- Ruthenium(III) catalyzed oxidation of propane-1,3-diol by potassium periodate was studied in aqueous perchloric acid medium.
- The reaction was found to be first order in oxidant and catalyst concentrations, and inverse fractional order in acid concentration. Substrate inhibition was also observed with increasing substrate concentration.
- Various reaction conditions like temperature, addition of salts, and acetic acid-water solvent composition were varied to determine their effects. Based on the kinetic data, a plausible reaction mechanism was proposed.Nef reaction
1) The Nef reaction involves the acid hydrolysis of primary or secondary nitroalkane salts, which produces carbonyl compounds such as aldehydes or ketones.
2) The reaction was first reported by J.U. Nef in 1894 and is generally used to convert nitroalkanes into the corresponding carbonyl compounds.
3) Over time, modified Nef reactions have been developed using oxidizing or reducing agents to improve the selectivity and functional group tolerance of the reaction. These allow synthesis of various biologically active compounds.
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
The Wagner-Meerwein rearrangement is an organic reaction that converts an alcohol to an olefin using an acid catalyst. It involves the formation of a carbocation intermediate followed by a 1,2-shift of a group to form a more stable carbocation. This is then deprotonated to form the olefin product. It can be used to rearrange highly branched compounds and reduce ring strain in cyclic compounds. Examples include the rearrangement of neopentyl alcohols and bicyclic terpene derivatives.
Chapter 2 Biocatalysts and Non-biological Catalysts.pptx
This chapter covers discussion about catalytic protein enzymes and the role of RNA enzymes and antibody enzymes
Al-Bashir 1994b WatRes
The document summarizes research on the biodegradation kinetics of three nitrogen-substituted naphthalenes (1-aminonaphthalene, 2-aminonaphthalene, and 1-amino-2-methylnaphthalene) under aerobic conditions in flooded soil. The researchers found that mineralization of the compounds proceeded in two phases - an initial fast phase followed by a slower second phase. Sorption of the compounds onto the soil followed hyperbolic isotherms described by the Langmuir model. Initial mineralization rates obeyed Michaelis-Menten kinetics and were directly proportional to aqueous concentrations, reaching a maximum at 100 μg/g soil slurry. The second phase mineralization rates were
Acidbasebook
This document provides an introduction to acid-base chemistry concepts. It discusses the Arrhenius, Brønsted-Lowry, and Lewis theories of acids and bases. The Arrhenius theory defined acids as producing H+ ions and bases as producing OH- ions upon dissolution. The Brønsted-Lowry theory improved upon this by defining acids as proton donors and bases as proton acceptors. The Lewis theory further generalized this to define acids as electron pair acceptors and bases as electron pair donors. The document also discusses the nature of ions in solution and the role of water as a solvent for acid-base reactions.
Schmidt reaction
The Schmidt reaction involves reacting an azide with a carbonyl compound like an aldehyde, ketone, or carboxylic acid under acidic conditions. This results in the formation of an amine or amide with the expulsion of nitrogen. The reaction was first reported in 1924 by Karl Friedrich Schmidt and involves the migration of a carbonyl substituent to the nitrogen atom of the azide. The Schmidt reaction is useful for synthesizing natural products and can be made enantioselective. Problems include site selectivity and potential tetrazole side product formation, though reaction conditions can be adjusted to control these issues.
Schmidt reaction
The Schmidt reaction involves reacting an azide with a carbonyl compound like an aldehyde, ketone, or carboxylic acid under acidic conditions. This results in the formation of an amine or amide with the expulsion of nitrogen. The reaction was first reported in 1924 by Karl Friedrich Schmidt and involves the migration of a carbonyl substituent to the nitrogen atom of the azide. The Schmidt reaction is useful for synthesizing amines, amides, nitriles, and lactams and has been applied to natural product synthesis. It can proceed intramolecularly and variants have been developed to achieve enantioselectivity.
SBrand_VLA4
This document summarizes the efficient synthesis of novel 3-aminocyclobut-2-en-1-ones, which are potent antagonists of VLA-4. The synthesis involves the condensation of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. This produces vinylogous amide derivatives in good yields. The cyclobuta-1,3-diones are prepared through cycloaddition of ketene intermediates, generated from acid chlorides, with various alkynes. The resulting 3-aminocyclobut-2-en-1-ones can then be functionalized at C-2 through reaction with electrophilic reagents
Rearrangement
This document summarizes several organic rearrangement reactions: the Cope rearrangement, Claisen rearrangement, and Curtius rearrangement. The Cope rearrangement involves the [3,3]-sigmatropic rearrangement of 1,5-dienes. The Claisen rearrangement is a carbon-carbon bond forming reaction that rearranges allyl vinyl ethers to γ,δ-unsaturated carbonyls. The Curtius rearrangement converts carboxylic acids to isocyanates through an acid azide intermediate. Mechanisms are provided for each reaction.
Witting reaction
The document discusses the Wittig rearrangement, specifically the [1,2]- and [2,3]- variants. The [1,2]-Wittig rearrangement involves the base-catalyzed rearrangement of an aryl alkyl ether to the corresponding secondary or tertiary alcohol via a 1,2-alkyl shift. The [2,3]-Wittig rearrangement involves the base-catalyzed sigmatropic rearrangement of an allylic ether to a homoallylic alcohol. Key features of each variant including substrate requirements, stereochemical outcomes, and reaction conditions are described. A variety of methods for generating the rearrangement anions are also discussed.
Neber rearrgment
The Neber rearrangement is a base-induced rearrangement of O-acylated ketoximes to the corresponding α-amino ketones. It was discovered in 1926 by Neber and Friedolsheim during their investigation of the Beckmann rearrangement. The Neber rearrangement has since become an important synthetic tool for synthesizing heterocycles that use amino ketones as intermediates. It proceeds through an alkoxide-induced rearrangement of the O-acylated ketoxime to form an α-amino ketone product. There are some limitations in that aldoximes do not undergo the rearrangement and substrates generally require a methylene group in the α-position.
Postdoctoral Research Summary
Adam B. Powell developed a heterogeneous catalyst composed of palladium, bismuth nitrate, and tellurium metal that promotes the aerobic oxidative esterification of aliphatic alcohols with high yields. The addition of bismuth and tellurium additives significantly increased the rate of product formation and overall yield compared to the catalyst without additives. The catalyst was shown to esterify a variety of activated and aliphatic alcohols, expanding the scope of this transformation. Future work includes adapting the catalyst for other oxidative reactions and developing a robust Pd-Bi-Te catalyst for flow applications.
MpCcP_JIB_2002
This document summarizes research on the effects of heme ring oxygenation on the structure and function of cytochrome c peroxidase (CcP). Specifically, it describes the synthesis of 4-mesoporphyrinone (mesopone) and its incorporation into CcP to form a hybrid protein called MpCcP. Testing found that MpCcP had similar peroxidase activity to wild-type CcP with cytochrome c, but varied activity with other substrates. Structural analysis via X-ray crystallography provided the first structural characterization of an oxygenated heme protein and found only the S-isomer of mesopone in the crystallized protein despite using a mixture of isomers.
IC Catalysis by FeSqMOF with pg nos
This document describes a study that uses an iron-squarate based 3D metal-organic framework (FeSq-MOF) as a heterogeneous catalyst for transforming tetrazines into oxadiazole derivatives at room temperature. The FeSq-MOF was found to efficiently catalyze the reaction of various tetrazine substrates to their corresponding oxadiazole products in yields ranging from 53-97% within 1-24 hours, depending on the substrate. Testing confirmed the heterogeneous nature of the catalysis and that no iron leaching occurred. The FeSq-MOF could be recycled for multiple reaction cycles with only a moderate decrease in yield after the third cycle. This new catalytic method provides a simple, mild, and
Oxidacion de etano a etileno y acido acetico con catalizadores MoV
This document discusses kinetics and mechanisms of partial oxidation of ethane to ethylene and acetic acid over molybdenum-vanadium (MoV) type catalysts. It provides background on previous studies that have suggested multi-phase catalysts are needed and that there are two catalytic sites, one for ethane oxidation and another for ethylene oxidation to acetic acid. The document then presents results of a new kinetics study investigating the effects of adding water to the feed on product formation. A reaction mechanism is proposed incorporating water participation through surface OH groups. A kinetic model is developed based on this new mechanism that satisfactorily predicts experimental results.
03 002
This study examined how pH and redox potential (Eh) influence the leaching of mercury from mining waste materials. Laboratory experiments were conducted by varying the pH from 2 to 12 and Eh under different gas purging conditions. Results showed that mercury concentration in leachates increased with rising pH until pH 10.65, above which it sharply decreased. The presence of iron significantly reduced mercury concentrations by 1/10th to 1/100th. Varying the Eh had little effect on mercury leaching, except when hydrogen peroxide was added to increase Eh, which sharply increased mercury levels. Alkaline and reduced conditions enhanced mercury solubility the most.
Similar to Rupe Rearrgment (19)
Substrate Inhibition in Ruthenium(III) Catalyzed Oxidation of Propane-1,3-dio...
Substrate Inhibition in Ruthenium(III) Catalyzed Oxidation of Propane-1,3-dio...
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
Chapter 2 Biocatalysts and Non-biological Catalysts.pptx
Chapter 2 Biocatalysts and Non-biological Catalysts.pptx
Oxidacion de etano a etileno y acido acetico con catalizadores MoV
Oxidacion de etano a etileno y acido acetico con catalizadores MoV
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Geographical Indicators
This document discusses geographical indications (GIs), including their definition, benefits, examples, registration process, challenges, and relationship to trademarks. Some key points:
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Errors PPt.pptx
Errors in analysis can be either determinate (systematic) or indeterminate (random). Determinate errors are caused by faults in the analytical procedure or instruments and result in consistently inaccurate results. Common sources of determinate error include faulty instrumentation, contaminated reagents, incorrect analytical methods, and analyst errors. Determinate errors can be identified by comparing results to a known standard or independent analytical method, and the source of the error must then be determined and corrected to improve accuracy.
Advance Green Chemistry.ppt
This document provides information about green chemistry. It discusses natural processes versus chemical processes and how green chemistry aims to make chemical processes more environmentally friendly. Some key points made include:
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- Natural processes are more environmentally friendly than traditional chemical processes which use toxic solvents and generate hazardous wastes.
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analytical dose.pptx
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Antibiotic Drug.ppt
This document discusses various classes of antibiotics including penicillins, cephalosporins, macrolides, tetracyclines, aminoglycosides, and quinolones. It describes their mechanisms of action, common uses, and potential adverse effects. Specifically, it provides details on common drugs in each class, how they work at the cellular level to kill bacteria, infections they can treat, and side effects to monitor like ototoxicity and nephrotoxicity. The document stresses the importance of obtaining cultures before treatment and monitoring patients for both therapeutic responses and unwanted reactions.
Assay In Drug Analysis.ppt
This document discusses different types of assays used in drug analysis, including chemical, immunological, microbiological, and bioassays. It provides details on various chemical assay techniques such as photometry, colorimetry, spectrophotometry, fluorimetry, flame photometry, and different types of chromatography. It also explains the principles, types, and techniques of immunoassays like ELISA, radioimmunoassay, and fluoroimmunoassay. Microbiological assays and characteristics of good assay methods are briefly covered as well.
bioassay.pptx
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Biological Catalyst.pptx
Dr. Gurumeet C Wadhawa discusses biocatalysts such as enzymes and microbes. Enzymes are mostly proteins that catalyze biochemical reactions in living cells and have unique three-dimensional shapes that fit reactants. They are produced commercially by isolating microbial strains that naturally produce the desired enzyme and optimizing fermentation conditions. Biocatalysts are classified into six types based on the reactions they catalyze. Important enzymes in the human body include digestive enzymes and DNA polymerases. Biocatalysts have various industrial applications in fields such as pharmaceuticals, food processing, and cosmetics.
Drug Discovery.pptx
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fda guidles.pptx
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Green Chemistry.ppt
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The document provides an overview of the pharmaceutical sector and its key business units and functions. It discusses:
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Mevolonic Acid.pptx
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Neighbouring Group Participation.pptx
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(ii) The pinacol-pinacolone rearrangement involves the migration of an alkyl group from one carbon to another after the loss of a leaving group from a vicinal diol. The migration is assisted by delocalization of the carbocation intermediate onto the oxygen atom.
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solid support.ppt
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Sonochemistry.pptx
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Spectrophotometry.pptx
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stability study.pptx
The document discusses stability studies of drug formulations. It defines stability as the ability of a drug product to remain within established specifications over time under storage and usage conditions. Stability testing is conducted to determine shelf life, recommended storage conditions, and suitability of packaging. The main types of drug degradation discussed are physical degradation (changes in appearance, solubility) and chemical degradation (hydrolysis, oxidation). Specific examples of each type of degradation are provided.
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Describing and Interpreting an Immersive Learning Case with the Immersion Cub...
Current descriptions of immersive learning cases are often difficult or impossible to compare. This is due to a myriad of different options on what details to include, which aspects are relevant, and on the descriptive approaches employed. Also, these aspects often combine very specific details with more general guidelines or indicate intents and rationales without clarifying their implementation. In this paper we provide a method to describe immersive learning cases that is structured to enable comparisons, yet flexible enough to allow researchers and practitioners to decide which aspects to include. This method leverages a taxonomy that classifies educational aspects at three levels (uses, practices, and strategies) and then utilizes two frameworks, the Immersive Learning Brain and the Immersion Cube, to enable a structured description and interpretation of immersive learning cases. The method is then demonstrated on a published immersive learning case on training for wind turbine maintenance using virtual reality. Applying the method results in a structured artifact, the Immersive Learning Case Sheet, that tags the case with its proximal uses, practices, and strategies, and refines the free text case description to ensure that matching details are included. This contribution is thus a case description method in support of future comparative research of immersive learning cases. We then discuss how the resulting description and interpretation can be leveraged to change immersion learning cases, by enriching them (considering low-effort changes or additions) or innovating (exploring more challenging avenues of transformation). The method holds significant promise to support better-grounded research in immersive learning.
Randomised Optimisation Algorithms in DAPHNE
Slides from talk:
Aleš Zamuda: Randomised Optimisation Algorithms in DAPHNE .
Austrian-Slovenian HPC Meeting 2024 – ASHPC24, Seeblickhotel Grundlsee in Austria, 10–13 June 2024
https://ashpc.eu/
Immersive Learning That Works: Research Grounding and Paths Forward
We will metaverse into the essence of immersive learning, into its three dimensions and conceptual models. This approach encompasses elements from teaching methodologies to social involvement, through organizational concerns and technologies. Challenging the perception of learning as knowledge transfer, we introduce a 'Uses, Practices & Strategies' model operationalized by the 'Immersive Learning Brain' and ‘Immersion Cube’ frameworks. This approach offers a comprehensive guide through the intricacies of immersive educational experiences and spotlighting research frontiers, along the immersion dimensions of system, narrative, and agency. Our discourse extends to stakeholders beyond the academic sphere, addressing the interests of technologists, instructional designers, and policymakers. We span various contexts, from formal education to organizational transformation to the new horizon of an AI-pervasive society. This keynote aims to unite the iLRN community in a collaborative journey towards a future where immersive learning research and practice coalesce, paving the way for innovative educational research and practice landscapes.
ESR spectroscopy in liquid food and beverages.pptx
With increasing population, people need to rely on packaged food stuffs. Packaging of food materials requires the preservation of food. There are various methods for the treatment of food to preserve them and irradiation treatment of food is one of them. It is the most common and the most harmless method for the food preservation as it does not alter the necessary micronutrients of food materials. Although irradiated food doesn’t cause any harm to the human health but still the quality assessment of food is required to provide consumers with necessary information about the food. ESR spectroscopy is the most sophisticated way to investigate the quality of the food and the free radicals induced during the processing of the food. ESR spin trapping technique is useful for the detection of highly unstable radicals in the food. The antioxidant capability of liquid food and beverages in mainly performed by spin trapping technique.
The debris of the ‘last major merger’ is dynamically young
The Milky Way’s (MW) inner stellar halo contains an [Fe/H]-rich component with highly eccentric orbits, often referred to as the
‘last major merger.’ Hypotheses for the origin of this component include Gaia-Sausage/Enceladus (GSE), where the progenitor
collided with the MW proto-disc 8–11 Gyr ago, and the Virgo Radial Merger (VRM), where the progenitor collided with the
MW disc within the last 3 Gyr. These two scenarios make different predictions about observable structure in local phase space,
because the morphology of debris depends on how long it has had to phase mix. The recently identified phase-space folds in Gaia
DR3 have positive caustic velocities, making them fundamentally different than the phase-mixed chevrons found in simulations
at late times. Roughly 20 per cent of the stars in the prograde local stellar halo are associated with the observed caustics. Based
on a simple phase-mixing model, the observed number of caustics are consistent with a merger that occurred 1–2 Gyr ago.
We also compare the observed phase-space distribution to FIRE-2 Latte simulations of GSE-like mergers, using a quantitative
measurement of phase mixing (2D causticality). The observed local phase-space distribution best matches the simulated data
1–2 Gyr after collision, and certainly not later than 3 Gyr. This is further evidence that the progenitor of the ‘last major merger’
did not collide with the MW proto-disc at early times, as is thought for the GSE, but instead collided with the MW disc within
the last few Gyr, consistent with the body of work surrounding the VRM.
8.Isolation of pure cultures and preservation of cultures.pdf
Isolation of pure culture, its various method.
Applied Science: Thermodynamics, Laws & Methodology.pdf
When I was asked to give a companion lecture in support of ‘The Philosophy of Science’ (https://shorturl.at/4pUXz) I decided not to walk through the detail of the many methodologies in order of use. Instead, I chose to employ a long standing, and ongoing, scientific development as an exemplar. And so, I chose the ever evolving story of Thermodynamics as a scientific investigation at its best.
Conducted over a period of >200 years, Thermodynamics R&D, and application, benefitted from the highest levels of professionalism, collaboration, and technical thoroughness. New layers of application, methodology, and practice were made possible by the progressive advance of technology. In turn, this has seen measurement and modelling accuracy continually improved at a micro and macro level.
Perhaps most importantly, Thermodynamics rapidly became a primary tool in the advance of applied science/engineering/technology, spanning micro-tech, to aerospace and cosmology. I can think of no better a story to illustrate the breadth of scientific methodologies and applications at their best.
Equivariant neural networks and representation theory
Or: Beyond linear.
Abstract: Equivariant neural networks are neural networks that incorporate symmetries. The nonlinear activation functions in these networks result in interesting nonlinear equivariant maps between simple representations, and motivate the key player of this talk: piecewise linear representation theory.
Disclaimer: No one is perfect, so please mind that there might be mistakes and typos.
dtubbenhauer@gmail.com
Corrected slides: dtubbenhauer.com/talks.html
11.1 Role of physical biological in deterioration of grains.pdf
Storagedeteriorationisanyformoflossinquantityandqualityofbio-materials.
Themajorcausesofdeteriorationinstorage
•Physical
•Biological
•Mechanical
•Chemical
Storageonlypreservesquality.Itneverimprovesquality.
Itisadvisabletostartstoragewithqualityfoodproduct.Productwithinitialpoorqualityquicklydepreciates
Katherine Romanak - Geologic CO2 Storage.pdf
Presented at June 6-7 Texas Alliance of Groundwater Districts Business Meeting
EWOCS-I: The catalog of X-ray sources in Westerlund 1 from the Extended Weste...
Context. With a mass exceeding several 104 M⊙ and a rich and dense population of massive stars, supermassive young star clusters
represent the most massive star-forming environment that is dominated by the feedback from massive stars and gravitational interactions
among stars.
Aims. In this paper we present the Extended Westerlund 1 and 2 Open Clusters Survey (EWOCS) project, which aims to investigate
the influence of the starburst environment on the formation of stars and planets, and on the evolution of both low and high mass stars.
The primary targets of this project are Westerlund 1 and 2, the closest supermassive star clusters to the Sun.
Methods. The project is based primarily on recent observations conducted with the Chandra and JWST observatories. Specifically,
the Chandra survey of Westerlund 1 consists of 36 new ACIS-I observations, nearly co-pointed, for a total exposure time of 1 Msec.
Additionally, we included 8 archival Chandra/ACIS-S observations. This paper presents the resulting catalog of X-ray sources within
and around Westerlund 1. Sources were detected by combining various existing methods, and photon extraction and source validation
were carried out using the ACIS-Extract software.
Results. The EWOCS X-ray catalog comprises 5963 validated sources out of the 9420 initially provided to ACIS-Extract, reaching a
photon flux threshold of approximately 2 × 10−8 photons cm−2
s
−1
. The X-ray sources exhibit a highly concentrated spatial distribution,
with 1075 sources located within the central 1 arcmin. We have successfully detected X-ray emissions from 126 out of the 166 known
massive stars of the cluster, and we have collected over 71 000 photons from the magnetar CXO J164710.20-455217.
SAR of Medicinal Chemistry 1st by dk.pdf
In this presentation include the prototype drug SAR on thus or with their examples .
Syllabus of Second Year B. Pharmacy
2019 PATTERN.
ESA/ACT Science Coffee: Diego Blas - Gravitational wave detection with orbita...
ESA/ACT Science Coffee: Diego Blas - Gravitational wave detection with orbita...Advanced-Concepts-Team
Presentation in the Science Coffee of the Advanced Concepts Team of the European Space Agency on the 07.06.2024.
Speaker: Diego Blas (IFAE/ICREA)
Title: Gravitational wave detection with orbital motion of Moon and artificial
Abstract:
In this talk I will describe some recent ideas to find gravitational waves from supermassive black holes or of primordial origin by studying their secular effect on the orbital motion of the Moon or satellites that are laser ranged.快速办理(UAM毕业证书)马德里自治大学毕业证学位证一模一样
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Assuming spherical symmetry and weak field, it is shown that if one solves the Poisson equation or the Einstein field
equations sourced by a topological defect, i.e. a singularity of a very specific form, the result is a localized gravitational
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spherical shell without any underlying mass. Moreover, a large-scale structure which exploits this solution by assembling
concentrically a number of such topological defects can establish a flat stellar or galactic rotation curve, and can also deflect
light in the same manner as an equipotential (isothermal) sphere. Thus, the need for dark matter or modified gravity theory is
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Rupe Rearrgment
- 1. BY Dr. Gurumeet.C.Wadhawa DEPARTMENT OF CHEMISTRY K. B. P. College,Vashi,Navimumbai MEYER-SCHUSTER AND RUPE REARRANGEMENT
- 2. In 1922, K.H. Meyer and K. Schuster reported that the attempted conversion of 1,1,3-triphenyl-2-propynol to the corresponding ethyl ether with concentrated sulfuric acid and ethanol afforded 1,3,3- triphenyl propenone, an α,β- unsaturated ketone. The authors showed that the use of other reagents such as acetic anhydride and acetyl chloride also brought about the same reaction. A few years later, H. Rupe and co-workers investigated the acid- catalyzed rearrangement of a large number of α-acetylenic (propargylic) alcohols. The acid-catalyzed isomerization of secondary and tertiary propargylic alcohols, via a [1,3]-shift of the hydroxyl group, to the corresponding α,β- unsaturated aldehydes or ketones is known as the Meyer-Schuster rearrangement.
- 7. Meyer-Schuster rearrangement. The general features of this transformation are: 1) when the substrate contains a terminal alkyne, the product is an aldehyde, whereas substrates containing disubstituted alkynes yield ketones; 2) the substrates, 2° or 3° propargylic alcohols, may not have a proton at their α-position so that the initial propargylic cation can isomerize to an allenyl cation, which provides the product carbonyl compound; 3) the rearrangement can be catalyzed by both protic and Lewis acids under anhydrous or aqueous conditions.
- 8. The related acid-catalyzed rearrangement of tertiary propargylic alcohols, via a formal [1,2]-shift of the hydroxyl group, yielding the corresponding α,β- unsaturated ketones is called the Rupe rearrangement. The most important features of this reaction are: 1) the product is always the α,β-unsaturated ketone regardless of the substitution of the triple bond; 2) the substrates are tertiary propargylic alcohols that have hydrogen atoms available at their α-position; 3) most often strong protic acids mixed with alcohol solvents are used to bring about the rearrangement, but certain Lewis acid such as mercury(II)-salts and even dehydrating agents (SOCl2, P2O5, etc.) were shown to be effective; 4) the nature of the acid catalyst does not affect the course of the rearrangement.
- 9. disadvantages of the above two rearrangements are: 1) certain substrates may give rise to a mixture of Rupe and Meyer-Schuster rearrangement products; 2) low yields are observed when the product (especially aldehydes) undergoes self-condensation, or is readily oxidized under the reaction conditions; 3) acid-sensitive functionalities in the substrate may give undesired elimination products; and 4) the initial propargylic cation occasionally undergoes Wagner-Meerwein or Nametkin rearrangement.
- 17. References 1. Rupe, H.; Kambli, E. Helv. Chim. Acta 1926, 9, 672. 2. Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429-438. (Review). 3. Hasbrouck, R. W.; Anderson Kiessling, A. D. J. Org. Chem. 1973, 38, 2103-2106. 4. Baran, J.; Klein, H.; Schade, C.; Will, E.; Koschinsky, R.; Bäuml, E.; Mayr, H. Tetrahedron 1988, 44, 2181-2184. 5. Barre, V.; Massias, F.; Uguen, D. Tetrahedron Lett. 1989, 30, 7389– 7392. 6. An, J.; Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R. W. J. Org. Chem. 1997, 62, 2505–2511. 7. Yadav, J. S.; Prahlad, V.; Muralidhar, B. Synth. Commun. 1997, 27, 3415-3418. 8. Takeda, K.; Nakane, D.; Takeda, M. Org. Lett. 2000, 2, 1903–1905. 9. Weinmann, H.; Harre, M.; Neh, H.; Nickisch, K.; Skötsch, C.; Tilstam, U. Org. Proc. Res. Dev. 2002, 6, 216-219. 10. Mullins, R. J.; Collins, N. R. Meyer–Schuster Rearrangement. In Name Reactions for Homologations-Part II; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 305-318. (Review). 11. Chang, Y.-J.; Wang, Z.-Z.; Luo, L.-G.; Dai, L.-Y. Chem. Papers 2012, 66, 3338.