Reactive intermediates in the bicyclo[3.1.0]hexyl and bicyclo[3.1.0]hexylidene systems. VI. Free-radical addition of methanethiol and methanethiol-d to bicyclo[3.1.0]hex-2-ene

Abstract

1-Methylcyclohexyl chloride (X) was prepared by the method of Russell26 from 1-methylcyclohexanol and thionyl chloride.

Free-Radical Rearrangements

“…In the case of 265, this unreactivity was originally attributed to conformational effects (779). When generated in solution at 130°C, 267 affords benzene via an electrocyclic ring opening (463). Some bicyclic cyclopropylallyls undergo rearrangements that can be formally regarded as pericyclic reactions.…”

The effect of alkyl substitution on the oxidative cleavage of alkylphenylmethanols by ceric ammonium nitrate

“…The radical attack by chlorine and bromine on methylcyclopropane also qualitatively indicates rate enhancement (68). These studies and others (68)(69)(70)(71)(72) illustrate the intense interest in the cyclopropyl methyl radical. The esr spectrum of the cyclopropylmethyl radical indicates it exists in a preferred bisected conform ation (73)(74).…”