Premium
Cation radical pericyclic reactions: Cyclopropanation
Author(s) -
Bauld Nathan L.,
Stufflebeme Gary W.,
Lorenz Kurt T.
Publication year - 1989
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.610020802
Subject(s) - cyclopropanation , pericyclic reaction , chemistry , ethyl diazoacetate , cyclopropane , regioselectivity , carbene , conjugated system , organic chemistry , photochemistry , medicinal chemistry , catalysis , ring (chemistry) , polymer
Triarylaminium salts smoothly catalyze the cyclopropanation of dienes, styrenes and tetrasubstituted alkenes by ethyl diazoacetate. The reactions are regioselective and, in the case of additions to conjugated dienes, cyclopropane‐periselective. A cation radical chain mechanism involving carbene transfer from ethyl diazoacetate to a substrate cation radical is proposed.