Novel S-Alkylation Products from "Isolated Thiamin Ylide" via Thiaminium Neothiaminthiolate Ion Pair

DOI: 10.1021/jo00289a017

Source and publish data:

Journal of Organic Chemistry p. 467 - 470 (1990)

Update date:2022-07-29

Topics:

Authors:

Sugimoto, Hirohiko

Ishiba, Teruyuki

Sato, Tomohiro

Nakai, Hiroshi

Hirai, Kentaro

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Article abstract of DOI:10.1021/jo00289a017

The ambident anion character of thiamin ylide was demonstrated by alkylation reactions of the "isolated thiamin ylide" under neutral or basic conditions.Alkylation with alkyl halides yielded S-alkyl derivatives of the yellow form of thiamin (pyrimidopyrimidine derivatives) instead of 2-alkylthiamin.These and previous results provide chemical evidence that thiamin ylide and thiaminium neothiaminthiolate (8) undergo a facile interconversion in EtOH.

Full text of DOI:10.1021/jo00289a017

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