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Unexpected Course of the Darzens Reaction of Phenyl Esters of α‐Chlorocarboxylic Acids with Carbonyl Compounds–A Novel One‐Step Synthesis of α‐Chloro‐β‐lactones
Author(s) -
Wedler Christine,
Kunath Annamarie,
Schick Hans
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199520281
Subject(s) - chemistry , alkyl , organic chemistry , lactone
The use of phenyl esters in lieu of alkyl esters drastically changes the course of the Darzens reaction of α‐chlorocarboxylates with carbonyl compounds. Instead of the usual glycidic esters, α‐chloro‐β‐lactones 1 are formed in good yields. These lactones are useful synthetic building blocks. R 1 = Me, Et, t Bu, Ph, PhCH 2 CH 2 ; R 2 = H, Me, Et; R 1 /R 2 = (CH 2 ) 4 , (CH 2 ) 5 .