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

doi:10.1021/jo00264a017

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English
Pages (from-to)	592-601
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	54
Issue number	3
DOIs	https://doi.org/10.1021/jo00264a017
State	Published - 1 Feb 1989

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

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.",

author = "Feldman, {Ken S.} and Come, {Jon H.} and Kosmider, {Benedict J.} and Smith, {Pamela M.} and Rotella, {David P.} and Wu, {Ming Jung}",

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T1 - Mechanistic and Preparative Studies of the Intramolecular Photocyclization of Methylated 2-(4-Pentenyl)tropones

AU - Feldman, Ken S.

AU - Come, Jon H.

AU - Kosmider, Benedict J.

AU - Smith, Pamela M.

AU - Rotella, David P.

AU - Wu, Ming Jung

PY - 1989/2/1

Y1 - 1989/2/1

N2 - 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.

AB - 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

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