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Synlett 2011(10): 1449-1453  
DOI: 10.1055/s-0030-1260562
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselectivity in Thermal Rhodium(II)-Catalysed Büchner-Type Reactions of Substituted Aryl Halides: Studies towards the Synthesis of Halide-Substituted Cycloheptatrienes

Emma E. Wyatt, Warren R. J. D. Galloway, David R. Spring*
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336362; e-Mail: spring@ch.cam.ac.uk;
Further Information

Publication History

Received 23 March 2011
Publication Date:
13 May 2011 (online)

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Abstract

The results of Büchner-type reactions of various substituted aryl halide derivatives with ethyl diazoacetate are presented, together with a discussion of factors affecting the regioselectivity of these processes.

Key words

Büchner reaction - regioselectivity - cycloaddition - carbenoids - rearrangement

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7

A full account of our computational modelling studies on the Büchner reactions described in this paper will be reported in due course.