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NITRENE
BEBETO G NAIR
199305
1ST MSC ANALYTICAL CHEMISTRY
率
Bebeto G Nitrenes 26/09/2019
Nitrenes
 Nitrogenous analogue of carbene
 Monovalent nitrogen species
 Contains no charge
 Electron deficient
 Electrophile
 Highly reactive
2
Singlet
SP 2 Hybridisation
STRUCTURE OF NITRENE
Triplet
SP Hybridisation
Bebeto G Nitrenes 26/09/2019
3
Stability
 Triplet > Singlet
 Presence of unpaired electrons in each orbital
 Only 33KJ/mol Energy
 Usually present in Ground state
Bebeto G Nitrenes 26/09/2019
4
Generation
 From acyl and alkyl Azides
 From sulphinylamine
 Insertion reaction
5
From acyl and alkyl azides
Bebeto G Nitrenes 26/09/2019
6
From sulphinylamine
Bebeto G Nitrenes 26/09/2019
7
Insertion reaction
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8
Important Name Reactions
 Beckmann Rearrangement Reaction
 Hoffman Bromamide Reaction
 Curtius Rearrangement Reaction
 Lossen Rearrangement Reaction
 Schmidt Rearrangement Reaction
Bebeto G Nitrenes 26/09/2019
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Beckmann Rearrangement Reaction
Bebeto G Nitrenes 26/09/2019
10
- Ernst Otto Bechmann
Hofmann Bromamide Reaction
Bebeto G Nitrenes 26/09/2019
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- August Wilhelm Von Hofmann
Curtius rearrangement
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- Theodor Curtius
Lossen rearrangement
Bebeto G Nitrenes 26/09/2019
13
- Wilhelm Lossen
Schmidt rearrangement
Bebeto G Nitrenes 26/09/2019
14
- Karl Friedrich Schmidt
Bebeto G Nitrenes 26/09/2019
率
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Nitrenes - Bebeto . G