123.202 Lecture 7 - alkenes
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123.202 Lecture 7 - alkenes

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123.202 alkenes

123.202 alkenes

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123.202 Lecture 7 - alkenes 123.202 Lecture 7 - alkenes Presentation Transcript

  • LECTURE SEVEN alkenes ©mugley@flickr
  • hyd rogenation of alkenes H2 Pd/C H H syn addition
  • ©Oberazzi@flickr
  • surface reaction H H H H H H
  • surface reaction H H H H H H
  • surface reaction H H H H H H H delivered from same face
  • ©e-magic@flickr
  • importance of stereochemistry ? H2 Pd/C ? H2 Pd/C
  • importance of stereochemistry H2 H H Pd/C Z-alkene meso cis achiral
  • importance of stereochemistry H2 H H Pd/C E-alkene chiral trans
  • example O O H O O OMe OH O O OH resiniferatoxin ©VT Jenny@Horticulture in the desert
  • example O O H O O OMe OH O O OH resiniferatoxin 1000x
  • example OAc OAc OBn H2 OBn 10% Pd/C H H O O O 99% O OTBS OTBS H H H H H H O O H O O OMe OH O O resiniferatoxin OH J. Am. Chem. Soc., 1997, 119, 12976
  • hyd rogenation of alkynes H2 H Pd/C H H H full reduction
  • partial Z-alkene reduction cis H2 Lindlar catalyst H H syn addition
  • ©wonderferret@flickr
  • catalyst poisoning Pd/CaCO3/Pb ©Grant and Caroline@flickr
  • partial E-alkene reduction trans Na NH3(l) H H anti addition
  • ©carbonNYC@flickr
  • Na NH3 Na e [NH3]n ©P.P.Edwards@Oxford University
  • mechanism e H NH2 H H e H NH2 H radical permits H isomerisation
  • S HO N O O OH O epothilone C example
  • S TBSO N O O OTBS O i. H2, Lindlar cat. ii. HF (79%) H H S HO N O O OH O
  • hydrohalogenation & acid-catalysed hydration X H X H
  • step 1 H X H X nucleophile step 2 electrophile X mechanism H
  • H step 1 H H O H O H H nucleophile step 2 electrophile H H O mechanism H
  • H step 1 H H O H O H H step 2 H O H H O H H O H H
  • remember electrons ©Aidan O'Sullivan@flickr attack δ+ or +