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Synthesis 2011(19): 3083-3088  
DOI: 10.1055/s-0030-1260164
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Mechanistic Insight into the Halogen Dance Rearrangement of Iodooxazoles

Nicolas Proust, Mathieu F. Chellat, James P. Stambuli*
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA
e-Mail: stambuli@chemistry.ohio-state.edu;
Further Information

Publication History

Received 2 July 2011
Publication Date:
08 August 2011 (online)

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Abstract

The lithium diisopropylamide mediated halogen dance reaction of 5-iodooxazoles to generate 4-iodooxazoles was studied. The mechanism of the reaction was investigated and compared to the reported mechanism for the halogen dance rearrangement of 5-bromooxazoles. Reaction conditions were optimized and yields of iodooxazole were improved to a synthetically useful level. The use of 2-(butylsulfanyl)-5-bromooxazole as an organic catalyst turned out to be the cornerstone for the success of this reaction.

Key words

halogen dance - oxazoles - halides - heterocycles - lithiation

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