Study of the reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride

Autor: Mikhno, S. D., Filippova, T. M., Kulachkina, N. S., Razumova, I. G., Zamureenko, V. A., Berezovskii, V. M.
Zdroj: Chemistry of Heterocyclic Compounds; February 1975, Vol. 11 Issue: 2 p155-158, 4p
Abstrakt: The reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride was studied. It was found that chlorosulfites are initially formed with retention of the configuration of the starting compound. 2-Substituted 3a,4,6,6a-tetrahydrothieno[3,4-d]oxazoline is formed from trans-4-acylamino-3-chlorosulfitothiophans by thermal reaction or in the presence of pyridine, whereas trans-4-acylamino-3-chlorothiophans are obtained from cis-4-acylamino-3-chlorosulfitothiophans; both reactions proceed with inversion of configuration.
Databáze: Supplemental Index
Externí odkaz: