Photochemistry of Bicycloalkyl Phenyl Ketones

Frederick D. Lewis; Richard W. Johnson; Ronald A. Rudenlb

doi:10.1021/ja00767a043

Photochemistry of Bicycloalkyl Phenyl Ketones

Frederick D. Lewis^*, Richard W. Johnson, Ronald A. Rudenlb

^*Corresponding author for this work

Chemistry

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

46 Scopus citations

Abstract

The photochemistry of several bicycloalkyl and cyclopentyl phenyl ketones has been investigated. The quantitative and stereoselective photochemical syntheses of a tricyclo[3.2.1.03′6]octane and tricyclo[3.3.1.02′7]-nonane are described. a-Methyl substituents are found to increase greatly the ratio of photocyclization to photoelimination products and to affect the reactivity of the carbonyl excited state toward 7-hydrogen abstraction. The large variation in the rate constants for secondary 7-hydrogen abstraction (2.5 X 106 to 1 X 1010 sec-1) for the ketones studied is attributed primarily to conformational factors.

Original language	English (US)
Pages (from-to)	4292-4297
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	94
Issue number	12
DOIs	https://doi.org/10.1021/ja00767a043
State	Published - Jun 1 1972

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Photochemistry of Bicycloalkyl Phenyl Ketones",

abstract = "The photochemistry of several bicycloalkyl and cyclopentyl phenyl ketones has been investigated. The quantitative and stereoselective photochemical syntheses of a tricyclo[3.2.1.03′6]octane and tricyclo[3.3.1.02′7]-nonane are described. a-Methyl substituents are found to increase greatly the ratio of photocyclization to photoelimination products and to affect the reactivity of the carbonyl excited state toward 7-hydrogen abstraction. The large variation in the rate constants for secondary 7-hydrogen abstraction (2.5 X 106 to 1 X 1010 sec-1) for the ketones studied is attributed primarily to conformational factors.",

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year = "1972",

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T1 - Photochemistry of Bicycloalkyl Phenyl Ketones

AU - Lewis, Frederick D.

AU - Johnson, Richard W.

AU - Rudenlb, Ronald A.

PY - 1972/6/1

Y1 - 1972/6/1

N2 - The photochemistry of several bicycloalkyl and cyclopentyl phenyl ketones has been investigated. The quantitative and stereoselective photochemical syntheses of a tricyclo[3.2.1.03′6]octane and tricyclo[3.3.1.02′7]-nonane are described. a-Methyl substituents are found to increase greatly the ratio of photocyclization to photoelimination products and to affect the reactivity of the carbonyl excited state toward 7-hydrogen abstraction. The large variation in the rate constants for secondary 7-hydrogen abstraction (2.5 X 106 to 1 X 1010 sec-1) for the ketones studied is attributed primarily to conformational factors.

AB - The photochemistry of several bicycloalkyl and cyclopentyl phenyl ketones has been investigated. The quantitative and stereoselective photochemical syntheses of a tricyclo[3.2.1.03′6]octane and tricyclo[3.3.1.02′7]-nonane are described. a-Methyl substituents are found to increase greatly the ratio of photocyclization to photoelimination products and to affect the reactivity of the carbonyl excited state toward 7-hydrogen abstraction. The large variation in the rate constants for secondary 7-hydrogen abstraction (2.5 X 106 to 1 X 1010 sec-1) for the ketones studied is attributed primarily to conformational factors.

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JF - Journal of the American Chemical Society

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ER -

Photochemistry of Bicycloalkyl Phenyl Ketones

Abstract

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