Isomerization of 3-pentyl-5-methyl-γ-sultine with iodine

Isomerization of 3-pentyl-5-methyl-1,2-oxathiolane-2-oxide in the presence of iodine is described. A mechanistic pathway which involves a ring-opening reaction by cleavage of the CO bond with or without epimerization at the sulfur atom is proposed, consistent with the stereochemical investigations....

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1999-04, Vol.40 (16), p.3159-3160
Main Authors: Yolka, S., Fellous, R., Lizzani-Cuvelier, L., Loiseau, M.
Format: Article
Language:English
Subjects:
2-oxathiolane-2-oxides
epimerization
iodine
isomerization
sultines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Isomerization of 3-pentyl-5-methyl-1,2-oxathiolane-2-oxide in the presence of iodine is described. A mechanistic pathway which involves a ring-opening reaction by cleavage of the CO bond with or without epimerization at the sulfur atom is proposed, consistent with the stereochemical investigations. A mechanism is proposed for the isomerization of 3-pentyl-5-methyl-γ-sultine in the presence of iodine, consistent with stereochemical investigations.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00416-5