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Tuning intramolecular carbenic insertions
Author(s) -
Moss Robert A.,
Liu Weiguo,
Ge ChuanSheng
Publication year - 1993
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610060611
Subject(s) - chemistry , intramolecular force , substituent , hydride , stereochemistry , crystallography , medicinal chemistry , hydrogen , organic chemistry
The 1,2‐carbenic hydride shift of neopentylmethoxycarbene was suppressed by the methoxy substituent. Thermally activated hydride shifts were observed with phenoxymethylmethoxycarbene and phenoxymethyltrifluoro‐ethoxycarbene, where appropriate potentiating substituents were introduced at both the migration origin and the migration terminus. Similarly, the 1,3‐CH insertion reaction of tert ‐butylfluorocarbene could be induced by thermal activation.