Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Marcin Palusiak,
• Heinz Heimgartner,
• Marta Denel-Bobrowska and
• Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

• derived from 5-mercapto-1H-tetrazoles was also examined. Keywords: 2,5-dihydro-1,3,4-thiadiazoles; enolizable 5-mercapto-1H-tetrazoles; insertion reactions; thiiranes; thiocarbonyl ylides; X-ray analysis; Introduction Cycloaddition reactions, including 1,3-dipolar cycloadditions, are considered as one

Dimerization reactions of aryl selenophen-2-yl-substituted thiocarbonyl S-methanides as diradical processes: a computational study

• Michael L. McKee,
• Grzegorz Mlostoń,
• Katarzyna Urbaniak and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 410–416, doi:10.3762/bjoc.13.44

• -methanides 1 belong to the class of S-centered 1,3-dipolar species, which were identified by Huisgen as reactive intermediates formed via nitrogen extrusion from 2,5-dihydro-1,3,4-thiadiazoles 2 [1][2]. In spite of the fact that several methods are reported for the preparation of these precursors, the most

• convenient access comprises the treatment of a C=S substrate with diazomethane or its derivatives. Depending on the substitution pattern, 2,5-dihydro-1,3,4-thiadiazoles 2 display different thermal stability. Whereas sterically bulky aliphatic substituents increase the temperature required for the