The Journal of Organic Chemistry

Photochemistry of naphthylmethyl halides. Direct and sensitized paths to homolytic and heterolytic carbon-halogen bond cleavage

GH Slocum, GB Schuster

Index: Slocum, Gregory H.; Schuster, Gary B. Journal of Organic Chemistry, 1984 , vol. 49, # 12 p. 2177 - 2185

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Citation Number: 49

Abstract

Photolysis of the 1-(halomethy1) naphthalenes (X= C1, Br, I) in methanol and in cyclohexane solution was investigated. Direct and sensitized irradiation leads to carbon- halogen bond cleavage. In methanol solution direct irradiation leads to products of carbon- halogen bond heterolysis, ie,(methoxymethyl) naphthalene, as well as products derived from bond homolysis. In cyclohexane only homolysis products are observed. The mechanism ...