An unexpected reaction of 2-vinyloxyethyl isothiocyanate with halocarboxylic acids

Autor: Nedolya, N. A., Papsheva, N. P., Afonin, A. V., Kukhareva, V. A., Kashik, T. V., Trofimov, B. A.
Zdroj: Russian Chemical Bulletin; February 1993, Vol. 42 Issue: 2 p310-314, 5p
Abstrakt: Reactions of 2-vinyloxyethyl isothiocyanate with aliphatic halocarboxylic acids give rise to their 1-(2-isothiocyanatoethoxy)ethyl esters in quantitative yields. An unusual rearrangement of 1-(2-isothiocyanatoethoxy)ethyl chloro(bromo)acetate and 3-bromopropanoate to 5-aza-7-chloro(bromo)-4-oxo-3-thiaheptanoic and to 6-aza-8-bromo-5-oxo-4-thiaoctanoic acids, respectively, was observed. Monohalocarboxylic acids and their esters were shown to readily alkylate l,3-oxazolidine-2-thione to form the same thiaheptanoic and thiaoctanoic acids and their esters.
Databáze: Supplemental Index