Photocycloadditions of benzophenone with 6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds. Di-.PI.-methane photorearrangement of the primary photocycloadducts.

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概要

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• The photocycloadditions of benzophenone with constrained divinylcyclopropanes such as 1,5-dimethyl- and 1,3,5-trimethyl-6-methylenetricyclo[3.2.1.0<SUP>2,7</SUP>]oct-3-en-8-ones, 5,8-dimethyl-9-methylenetricyclo[3.3.1.<SUP>2,8</SUP>] non-3-en-6-one, 5,8-dimethyl-9-methylenetricyclo[3.3.1.0<SUP>2,8</SUP>]non-3-en-7-one, and their corresponding alcohols were investigated. In no cases, was oxetane formation observed but the formal [2+6] cycloaddition which originates from the cleavage of a cyclopropane ring was observed. In the case of the compounds which have a carbonyl function, benzophenone sensitized di-π-methane or oxadi-π-methane rearrangement of the primary photocycloadducts was observed. The mechanism of the formation of photoproducts is discussed with emphasis on (i) the nature of the intermediates having tricyclo[3.2.1.0<SUP>2,7</SUP>]oct-3-en-6-yl and tricyclo[3.3.1.0<SUP>2,8</SUP>]non-3-en-9-yl radicals, (ii) the regioselectivity of the di-π-methane or oxadi-π-methane rearrangement of the primary photocycloadducts.

• 公益社団法人 日本化学会の論文

著者

• Nitta Makoto

  Department Of Applied Pharmacology Toyama Medical And Pharmaceutical University

• Sugiyama Hiroshi

  Department Of Chemistry Faculty Of Science

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