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Synthesis 2010(16): 2771-2775
DOI: 10.1055/s-0030-1258148
DOI: 10.1055/s-0030-1258148
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Bismuth Compounds in Organic Synthesis: Synthesis of Dioxanes, Dioxepines, and Dioxolanes Catalyzed by Bismuth(III) Triflate
Further Information
Received
8 March 2010
Publication Date:
02 July 2010 (online)
Publication History
Publication Date:
02 July 2010 (online)
Abstract
A simple method for the synthesis of 1,3-dioxolanes from carbonyl compounds has been developed using 1,2-bis(trimethylsilyloxy)ethane in the presence of bismuth(III) triflate as a catalyst. The bismuth(III) triflate catalyzed synthesis of a range of dioxanes and dioxepines has also been developed. In these latter cases, the carbonyl compound is treated with a diol, and triethyl orthoformate is used as a water scavenger. All these methods avoid the use of a Dean-Stark trap.
Key words
aldehydes - ketones - protection - cyclic acetals - 1,2-bis(trimethylsilyloxy)ethane
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Most bismuth(III) compounds have an LD50 value that is comparable to or even less than that of NaCl (see ref. 9d).