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 Rotella, Ming Jung Wu

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27 Citations (Scopus)

Abstract

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
Volume54
Issue number3
DOIs
StatePublished - 1 Feb 1989

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Stereoselectivity
Regioselectivity
Stereoisomerism
Irradiation
tropone

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Feldman, Ken S. ; Come, Jon H. ; Kosmider, Benedict J. ; Smith, Pamela M. ; Rotella, David ; Wu, Ming Jung. / Mechanistic and Preparative Studies of the Intramolecular Photocyclization of Methylated 2-(4-Pentenyl)tropones. In: Journal of Organic Chemistry. 1989 ; Vol. 54, No. 3. pp. 592-601.
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abstract = "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.",
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Mechanistic and Preparative Studies of the Intramolecular Photocyclization of Methylated 2-(4-Pentenyl)tropones. / Feldman, Ken S.; Come, Jon H.; Kosmider, Benedict J.; Smith, Pamela M.; Rotella, David; Wu, Ming Jung.

In: Journal of Organic Chemistry, Vol. 54, No. 3, 01.02.1989, p. 592-601.

Research output: Contribution to journalArticleResearchpeer-review

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