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Sulfonamide-Trapping Reactions of Thermally Generated Benzynes.

ABSTRACT: Reactions of tethered, tertiary sulfonamides with thermally generated benzynes are reported. Typically, the N-S bonds in the substrates cleave, and saturated heterocycles [tetrahydroquinolines ( n = 2) and indolines ( n = 1)] are formed. The process is accompanied by either sulfonyl transfer or desulfonylation from a zwitterionic intermediate, with the favored pathway being largely dependent upon the size (5- vs 6-membered) of the N-containing ring in the zwitterion.

SUBMITTER: Wang Y

PROVIDER: S-EPMC6348468 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Sulfonamide-Trapping Reactions of Thermally Generated Benzynes.

Wang Yuanxian Y Zheng Lianyou L Hoye Thomas R TR

Organic letters 20181105 22

Reactions of tethered, tertiary sulfonamides with thermally generated benzynes are reported. Typically, the N-S bonds in the substrates cleave, and saturated heterocycles [tetrahydroquinolines ( n = 2) and indolines ( n = 1)] are formed. The process is accompanied by either sulfonyl transfer or desulfonylation from a zwitterionic intermediate, with the favored pathway being largely dependent upon the size (5- vs 6-membered) of the N-containing ring in the zwitterion. ...[more]

PMID: 30394095

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