Volume 27, Issue 18
Isocyclic Compounds
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ChemInform Abstract: Base-Catalyzed Ring Openings of Benzocyclobutenones and -ols.

J. C. BRADLEY

J. C. BRADLEY

Dep. Chem., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.

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T. DURST

T. DURST

Dep. Chem., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.

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First published: April 30, 1996

Abstract

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ChemInform Abstract

The base-catalyzed ring opening of E- and Z- benzylidenebenzocyclobutenones and -ols is studied in protic and aprotic solvents. Stilbenes are formed by cleavage of the C-1/C-2 bond mainly under retention of stereochemistry. Reaction of (XV) or its E- isomer with MeLi in THF proceeds with isomerization to give the alcohols (XVII) and (XVIII) in both cases.

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