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Synlett 1997; 1997(SI): 461-462
DOI: 10.1055/s-1997-6150
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A New Synthetic Method for Cyclic Allenes and Acetylenes. Cleavage of a C-C Bond Directed by a Silyl Group

Masaharu Sugai, Keiji Tanino, Isao Kuwajima*
  • *Department of Chemistry, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
31 December 2000 (online)

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A new synthetic method for medium-sized cyclic allenes and acetylenes was developed on the basis of a C-C bond cleavage directed by a silyl group. An enol triflate derived from 6-(silylmethyl)-10-siloxybicyclo[4.4.0]decan-2-one was heated at 150 °C in DMF to afford ten-membered allene in good yield. A cyclodecyne derivative was also prepared from the regioisomeric enol triflate.

fragmentation - enol triflate - allene - actylene - medium-sized ring