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Issue 5, 1994
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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.

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Article type: Paper
DOI: 10.1039/P19940000485
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 485-486

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

    T. Hudlicky and B. P. McKibben, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 485
    DOI: 10.1039/P19940000485

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