The photo-cycloaddition of vinyl acetate to benzene and its simple derivatives

Functionalisation of the dihydrosemibullvalene skeleton

Andrew Gilbert, Mohd Wahid Bin Samsudin

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The photo-reaction of vinyl acetate with benzene yields both ortho- and meta-cycloadducts in an initial ratio of 1 : 7. The ortho-product has endo-stereochemistry but a mixture of regio- and stereo-isomers result from the meta-cycloaddition. Base-catalysed hydrolysis of the meta-adducts yields the corresponding alcohols, whereas acid treatment gives 2-substituted derivatives of bicyclo[3.3.0]octa-3,7-diene. The photo-reaction of vinyl acetate with toluene, anisole, fluorobenzene, and p-xylene also yields meta-cycloadducts: the results are discussed in terms of previously proposed reaction intermediates.

Original languageEnglish
Pages (from-to)1118-1123
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1980
Externally publishedYes

Fingerprint

Cycloaddition
Benzene
Isomers
Fluorobenzenes
Derivatives
Reaction intermediates
Stereochemistry
Toluene
Hydrolysis
Alcohols
Acids
vinyl acetate
4-xylene
anisole

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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