New cycloaddition chemistry of 1-chloro-5,6-cis-isopropylidenedioxycyclohexa-1,3-diene derived from the oxidation of halogenobenzenes by Pseudomonas putida 39D

Abstract

Several new modes of cycloadditions of 1-Chloro-5, 6-cis-isopropylidenedioxycyclohexa-1, 3-diene 1 have been investigated. Under thermal conditions, benzoquinone, naphthoquinone and benzyne react with 1 to give [4 + 2] cycloadducts resulting from addition to the less hindered face and in an endo fashion. Under photolysis conditions, benzoquinone undergoes a hetero [4 + 2] cyclization with the diene. Generation of nitrile oxide in the presence of the diene leads to a stereoselective [3 + 2] cycloaddition.