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The Stereo- and Regio-specific Formation of 11-Oxatetracyclo2,4.03,7> undeca-5,9-dienes by the Substituent-directed Photocycloaddition of Furan to the Benzene Ring

DOI: 10.1039/P19900000931

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 931 - 935 (1990)

Update date:2022-08-04

Topics:

Authors:

Gilbert, AndrewGilbert, Andrew

Rodwell, Paul W.Rodwell, Paul W.

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Article abstract of DOI:10.1039/P19900000931

Furan undergoes specific 2,5-2',6'(meta)-photocycloaddition to benzonitrile, the toluonitriles, phenylacetylene, and 1-phenylpropyne. 2-Phenylpropene yields exclusively a <2? + 2?> cycloadduct with furan whereas both types of addition occur with styrene.In contrast, 1,4-2',5'(para)-photocycloaddition is the sole or principal reaction from 254 nm irradiation of isoprene, 2,3-dimethylbuta-1,3-diene, or 2,3-dimethoxybuta-1,3-diene with benzonitrile; only with the fixed cis-1,3-diene, 1,2-dimethylene cyclohexane, is the meta-cycloadduct formed in significant amounts.The control over the regio- and stereo-chemistries of the meta-cycloaddition is discussed in terms of substituent stabilization of the developing polarity in the electronically excited aromatic ring on approach of the addends and secondary orbital interactions.

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