Mechanistic and Preparative Studies of the Intramolecular Photocyclization of Methylated 2-(4-Pentenyl)tropones

Ken S. Feldman, Jon H. Come, Benedict J. Kosmider, Pamela M. Smith, David P. Rotella, Ming Jung Wu

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Irradiation of various methylated 2-(4-pentenyl)tropones affords regioisomeric formal[6π+2πand[87π + 2π]cycloadducts. The cyclooctadiene-containing [6π + 2π]adductsare produced as mixtures of stereoisomers. A self-consistent mechanistic scheme based upon evidence accumulated through the study of regioselectivity and stereoselectivity as a function of reaction conditions has been proposed. This mechanism includes several discrete intermediates en route to the final cycloadducts. Attempts to functionalize [6π + 2π] cycloadducts through vinyllithium addition led to unconventional products through unanticipated reaction pathways.

Original languageEnglish
Pages (from-to)592-601
Number of pages10
JournalJournal of Organic Chemistry
Issue number3
Publication statusPublished - 1 Feb 1989


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