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Synthesis 2009(3): 385-388
DOI: 10.1055/s-0028-1083308
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
Further Information
Received
20 August 2008
Publication Date:
09 January 2009 (online)
Publication History
Publication Date:
09 January 2009 (online)
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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