On the mechanism of the meta photocycloaddition of ethylenes to benzenoid compounds
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1314-1318
- https://doi.org/10.1039/p19800001314
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.Keywords
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