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On the mechanism of the meta photocycloaddition of ethylenes to benzenoid compounds

Mike Dadson,  Andrew Gilbert  and  Peter Heath 

Abstract

cis-Cyclo-octene undergoes locoselective meta photocycloaddition to isopropylbenzene, t-butylbenzene, p-methylcumene, anisole, and p-methylanisole. The results are discussed in terms of substituent stabilisation of the intermediates produced either by meta ethylene cycloaddition to the S1 arene or by meta bonding in the photoexcited benzene derivative. The mechanistic pathway preferred appears to be influenced by steric effects of the arene and ethylene substituents.

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Article type: Paper
DOI: 10.1039/P19800001314
Citation: J. Chem. Soc., Perkin Trans. 1, 1980,0, 1314-1318
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    On the mechanism of the meta photocycloaddition of ethylenes to benzenoid compounds

    M. Dadson, A. Gilbert and P. Heath, J. Chem. Soc., Perkin Trans. 1, 1980, 0, 1314
    DOI: 10.1039/P19800001314

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