Ontology highlight
ABSTRACT:
SUBMITTER: Mereshchenko AS
PROVIDER: S-EPMC4419510 | biostudies-literature | 2015
REPOSITORIES: biostudies-literature
Mereshchenko Andrey S AS Ivanov Alexey V AV Baranovskii Viktor I VI Mloston Grzegorz G Rodina Ludmila L LL Nikolaev Valerij A VA
Beilstein journal of organic chemistry 20150420
The 1,3-dipolar cycloaddition of acyclic 2-diazo-1,3-dicarbonyl compounds (DDC) and thioketones preferably occurs with Z,E-conformers and leads to the formation of transient thiocarbonyl ylides in two stages. The thermodynamically favorable further transformation of C=S ylides bearing at least one acyl group is identified as the 1,5-electrocyclization into 1,3-oxathioles. However, in the case of diazomalonates, the dominating process is 1,3-cyclization into thiiranes followed by their spontaneou ...[more]