75681-96-8Relevant academic research and scientific papers
Electrophilic additions to strained alkenes. II. The reaction of benzeneselenenyl chloride with tricyclo2,5>deca-3,7-diene derivatives
Garratt, Dennis G.,Ryan, Dominic M.,Kabo, Ann
, p. 2329 - 2339 (2007/10/02)
The reactions of benzeneselenenyl chloride with three derivatives of tricyclo2,5>deca-3,7-diene have been investigated in four solvent systems: methylene chloride, acetic acid, acetic acid/LiClO4, and methanol.Under conditions of kinetic control only products of exo-anti attack upon the cyclobutene moiety are isolable when the solvent system is methylene chloride or acetic aicd.This observation also holds in acetic acid/LiClO4 except in the case of dimethyl tricyclo2,5>deca-3,7,9-triene-7,8-dicarboxylate where the major product is that of cross-bonding with solvent incorporation.In methanol products of solvent incorporation, transannular cross-bonding and lactonization (where possible) are observed.A general mechanistic scheme is proposed to account for these observations in accord with earlier results for the analogous arenesulphenylations.
