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Paper | Regular issue | Vol 34, No. 11, 1992, pp.2095-2108
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6105
Approaches to the Generation of 2,3-Indolyne

Samuel C. Conway and Gordon W. Gribble*

*Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, U.S.A.

Abstract

Several unsuccessful attempts to generate and trap 1-phenylsulfonyl-2,3-indolyne (4) from 2-lithio-3-bromo-1-phenylsulfonylindole (9) and 2-lithio-3-iodo-1-phenylsulfonylindole (12), generated by different methods, are described. The remarkable stability of 9 and 12 towards elimination parallels previous observations involving the stability of 2-lithio-3-bromobenzo[b]furan and other ortho-metalated halogenated five-membered ring heterocycles.