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Internal Addition of Ketocarbenes to Conjugated Double Bonds
Author(s) -
Becker D.,
Loewenthal H. J. E.
Publication year - 1972
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197200040
Subject(s) - chemistry , conjugated system , hydrogenolysis , cyclopropane , double bond , ring (chemistry) , ketone , derivative (finance) , organic chemistry , stereochemistry , catalysis , polymer , financial economics , economics
Abstract The internal, copper‐catalysed, addition of keto‐carbenes (generated from a diazoketone group) to a double bond conjugated either to a ketone or carboxylic ester function has been found to be a feasible preparative reaction in selected cases. This, together with the facile and regiospecific hydrogenolysis of the resulting 1,2‐dicarbonyl cyclopropane intermediate, appear to constitute a convenient route to multifunctional bridged‐ring systems.