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Synthesis 2014; 46(05): 613-620
DOI: 10.1055/s-0033-1340595
DOI: 10.1055/s-0033-1340595
paper
An Efficient and Convenient Protocol for the Synthesis of 1,1-Difluoro-6-nitro-2,3-dihydro-1H-indene Derivatives
Further Information
Publication History
Received: 15 September 2013
Accepted after revision: 12 December 2013
Publication Date:
23 January 2014 (online)
Abstract
A convenient and efficient synthesis of gem-difluorinated compounds is reported. The synthetic route toward various 2-substituted and 3-substituted 1,1-difluoro-6-nitro-2,3-dihydro-1H-indene derivatives is described starting from commercially available indanone. The key gem-difluorination step is accomplished in good yield by treatment of in situ generated bromine fluoride (BrF) with a dithioketal. A plausible mechanism discussing the competition between substitution and elimination is provided to rationalize the outcome of the reactions of the 3-brominated compounds with different amines.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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