Photochemical preparation of highly functionalized 1-indanones

P Wessig, C Glombitza, G Müller…

Index: Wessig, Pablo; Glombitza, Clemens; Mueller, Gunnar; Teubner, Janek Journal of Organic Chemistry, 2004 , vol. 69, # 22 p. 7582 - 7591

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Citation Number: 52

Abstract

A series of o-alkylphenyl alkyl ketones 1 were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-π* excitation followed by a 1, 5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1, 4-diradicals are subject to a very rapid ...

~79%

~95%

~84%

~71%

~40%

~90%

~62%

~54%

~40%

~90%

~43%

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