The photochemical reaction of benzene with ethylenes

Studies with allyl compounds, enamines, vinyl sulphide, and 5,6-dichlorobicyclo-[2.2.1 ]hept-2-ene

Andrew Gilbert, M. Wahid Bin Samsudin, Grahame N. Taylor, Steve Wilson

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Benzene undergoes regio- and stereo-selective meta photocycloaddition to methyl but-3-enoate and pent-1-en-4-ol but methyl allyl ketone and NN-dimethylallylamine yield only products of the addend; likewise irradiation of benzene with enamines or methyl vinyl sulphide at 254 nm does not yield photoadducts. The meta photocycloadducts of benzene with methyl but-3-enoate and vinyl acetate and the ketones obtained by oxidation of the adducts from pent-1-en-4-ol are all essentially photostable and do not undergo Norrish Type II eliminations. The dechlorination products of the meta photocycloaddition of 5,6-trans-dichlorobicyclo[2.2.1]hept-2-ene and benzene undergo a retro-Diels-Alder addition at high temperatures, but the C8H 8 isomer formed is cyclo-octatetraene.

Original languageEnglish
Pages (from-to)1225-1229
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1980
Externally publishedYes

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Ethylenes
Allyl Compounds
Photochemical reactions
Sulfides
Benzene
Ketones
Dechlorination
Isomers
Irradiation
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

The photochemical reaction of benzene with ethylenes : Studies with allyl compounds, enamines, vinyl sulphide, and 5,6-dichlorobicyclo-[2.2.1 ]hept-2-ene. / Gilbert, Andrew; Bin Samsudin, M. Wahid; Taylor, Grahame N.; Wilson, Steve.

In: Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 1225-1229.

Research output: Contribution to journalArticle

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