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Synthesis 2009(3): 385-388  
DOI: 10.1055/s-0028-1083308
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Ring Contraction of 1,2-Dihydronaphthalenes Promoted by Thallium(III) in Acetonitrile: A Diastereoselective Approach to Indanes

Helena M. C. Ferraz, Vânia M. T. Carneiro, Luiz F. Silva*
Instituto de Química, Universidade de São Paulo, CP 26077, CEP 05513-970, São Paulo SP, Brazil
e-Mail: luizfsjr@iq.usp.br;
Further Information

Publication History

Received 20 August 2008
Publication Date:
09 January 2009 (online)

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Abstract

trans-1,3-Disubstituted indanes are conveniently accessed by a stereoselective ring contraction of 1,2-dihydronaphthalenes upon treatment with thallium(III) nitrate (TTN) in acetonitrile. Under­ these conditions, the oxidative rearrangement of either di- or trisubstituted double bonds is possible.

Key words

thallium(III) nitrate - carbocycles - indanes - ring contractions - oxidative rearrangements

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