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The Photochemical Reactions of Benzene with 1,2-, 1,3-, and 1,4-Dienes

DOI: 10.1039/P19800002425

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2425 - 2434 (1980)

Update date:2022-08-04

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Authors:

Berridge, John C.Berridge, John C.

Forrester, JohnForrester, John

Foulger, Brian E.Foulger, Brian E.

Gilbert, AndrewGilbert, Andrew

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Article abstract of DOI:10.1039/P19800002425

The photocycloaddition reactions of benzene with 1,2-, 1,3-, and 1,4-dienes are described.Propa-1,2-diene (allene) and cyclonona-1,2-diene are unique among hydrocarbon ethylenic systems since 1,2-para-cycloaddition to the benzene ring is the major mode of reaction.The meta-cycloaddition of 1,2-dienes is regiospecific and this is accounted for by a mechanism involving prior meta-bonding in the arene leading to a polarised prefulvene species which undergoes 1,2-addition to the diene.The conformationally fixed cis-diene 1,2-dimethylenecyclohexane undergoes selective 1,4-para and 1,4-meta-photocycloaddition to benzene whereas the reaction with 3-methylenecyclohexene is of low yield and non-selective giving diene dimers, substitution products, and adducts.Penta-1,4-diene and cyclohexa-1,4-diene yield 1,2-meta-cyclo-adducts with benzene, and evidence is presented for formation of 1,2-para-cycloadducts from each system: diene dimers are also produced in the latter case but solutions of bicyclo<2.2.1>hepta-2,5-diene in benzene are essentially inert photochemically.

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