( E )‐ und ( Z )‐Enole von β‐Ketocarbonsäureamiden | Zendy

Wengenroth Horst | Zendy; Meier Herbert | Zendy

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( E )‐ und ( Z )‐Enole von β‐Ketocarbonsäureamiden

Author(s) -

Wengenroth Horst,

Meier Herbert

Publication year - 1990

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19901230633

Subject(s) - chemistry , steric effects , amide , stereochemistry , medicinal chemistry , primary (astronomy) , ammonia , chelation , organic chemistry , physics , astronomy

(E)‐ and (Z)‐Enols of β‐Ketocarboxylic Acid Amides Reaction of dimesitoyldiazomethane ( 1 ) with ammonia ( 3a ), primary and secondary amines ( 3b – o and 3p – v , respectively) leads to the completely enolized amides 4a – v . Besides the chelated Z configuration the unusual E isomer exists in the most cases, too. The Z/E distribution in the equilibrium depends on the steric and electronic effects present in the amide group CONR 2 R 3 and on the solvent.

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