this slide about NEF reaction and its use in a chemistry

1. NEF REACTION AND ITS
APPLICATIONS
PRESENTED BY
Shantanu gupta
4th sem. M. Tech(PHARM)
Pharmaceutical Technology (Process Chemistry )

2. FLOW OF PRESENTATION
•INTRODUCTION
•MECHANISM
•MODIFIED NEF REACTIONS
•APPLICATIONS
•CONCLUSION
2

3. INTRODUCTION
Interconversion of functional groups represents an important
aspect in every process leading to the synthesis of structurally
defined compounds
Nef reaction involves acid hydrolysis of a salt of primary or
secondary nitroalkane to yield carbonyl compounds
It was first reported by Nef in 1894
3

4. GENERAL TRANSFORMATIONS OF NITRO
GROUP4
Tetrahedron, 2004 ,60 ,1017–1047.

5. HISTORY
5
Nef reaction is named after the John
Ulric Nef
He was graduated from harvard
university
The discovery of nef reaction and
papers concerned with the divalent
carbon are his major acheivements
June 14, 1862 – August 13,
1915

6. MECHANISM
6

7. 7
Side reactions
 Self condensation
 Dimerization
 Formation of pseudonitroles
J. Am. Chem. Soc. 1955, 77 ,2622

8. 8
 Dehydration
 Nitrocompounds which fail to react under nef conditions
J. Am. Chem. Soc. 1948, 70, 746

9. 9
MODIFIED NEF REACTIONS

10. 10
OXIDATIVE METHODS
DMD
Synlett 1998, 1335

11. 11
Oxone
Synth. Commun. 1998, 28, 3054
MECHANISM

12. 12
Mc murry method
REDUCTIVE METHODS
J. Org. Chem. 1973, 38, 4367

13. 13
J. Org. Chem. 1973, 38, 4367.
MECHANISM

14. 14
Other methods
Tetrahedron Lett. 2002, 43, 5233

15. 15
APPLICATIONS

16. 16
In carbohydrate chemistry
Used as chain extension method of aldoses
J. Biol. Chem. 1949, 180,55-58

17. 17
Synthesis of α-amino acids
Tetrahedron Lett. 1999, 40, 4449

18. 18
Synthesis of allylrethrone
It is an important component of insecticidal pyrethroid
Synthesis. 1993, 687
18

19. 19
Synthesis of β-lactum building blocks
J. Org. Chem. 1990, 55, 2070

20. Conclusion
 Nef reaction dates back a century ago but still it has
significance due to its applicability in conversion of
nitrocompounds to carbonyl compounds
 Modified nef reactions uses oxidising and reducing
agents which helps in the synthesis of various biologically
active compounds
 It also has applications in carbohydrate chemistry as a
chain-extension method of aldoses
20

21. 21