Addition of Dichloro- and Dibromocarbene to 1,2-Diphenylcyclobutene

Addition of Dichloro- and Dibromocarbene to 1,2-Diphenylcyclobutene

1,2-Diphenylcyclobutene (7) was reacted with dibromo- and dichlorocarbene, both generated via three different methods. 1,3-Diphenyl-2-halocyclopenta-1,3-dienes 12 were isolated which result from addition of the dihalocarbenes to the cyclobutene double bond of 7. A cationic cyclopropyl-allyl rearrang...

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Bibliographic Details
Published in:Chemistry letters Vol. 29; no. 3; pp. 246 - 247
Main Authors: Wagner, Robert A, Weber, Jürgen, Brinker, Udo H
Format: Journal Article
Language:English
Published: Tokyo The Chemical Society of Japan 01-03-2000
Chemical Society of Japan
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Summary:1,2-Diphenylcyclobutene (7) was reacted with dibromo- and dichlorocarbene, both generated via three different methods. 1,3-Diphenyl-2-halocyclopenta-1,3-dienes 12 were isolated which result from addition of the dihalocarbenes to the cyclobutene double bond of 7. A cationic cyclopropyl-allyl rearrangement (CCA) in gem-dihalobicyclopentanes 8 leads to 2,3-dihalocyclopentenes 9, which under the reaction conditions are dehydrohalogenated to 12. A second carbene addition and rearrangement afford aromatic compounds 11 and 16.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2000.246