K. Miyawaki, Hitomi Suzuki, H. Morikawa
Sep 27, 2004
Citations
0
Influential Citations
6
Citations
Journal
Organic & biomolecular chemistry
Abstract
When stirred with powdered samarium and iodine in methanol at ice-cold temperature, ethyl 1,2,3-thiadiazole-4-carboxylate 5 underwent unusual reduction involving the dimeric ring enlargement with a sulfur addition, giving dimethyl 1,2,5-trithiepan-4,6-dicarboxylates 7a,b as a cis/trans-isomeric mixture in acceptable yield. The 1,2,3-thiadiazole ring of 5 proved to resist reduction by ordinary reducing agents, where the only choice in most cases was either recovery of the unchanged substrate or decomposition to an intractable mixture of unidentified products and tar.