Generation of 2-Chloronaphthalene-1,3-diyl

Article abstract of DOI:10.1021/jo01311a017

Reaction of 1-bromo-3,4-benzo-6,6-dichlorobicyclo<3.1.0>hexane with potassium tert-butoxide in tetrahydrofuran yields 2-chloronaphthalene along with nine other naphthalenes which result from solvent incorporation or reaction with nucleophile (Br^-, Cl^-, t-BuO^-).Use of tetrahydrofuran-d8 as the solvent leads to the incorporation of two deuterium atoms into the chloronaphthalene.This result is interpreted in terms of a 1,3-dehydronaphthalene opening to the diradical, followed by abstraction of deuterium atoms from the solvent.The products which result from incorporation of solvent would then arise by dimerization of radical pairs.The remaining products are thought to arise from nucleophilic addition to the closed form of the dehydronaphthalene.