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

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

The in situ-generated thiocarbonyl S-methanides (thiocarbonyl ylides), derived from cycloaliphatic thioketones, are efficiently trapped by enolizable 1-substitued 5-mercapto-1H-tetrazoles and formation of the corresponding N–H or S–H insertion products, i.e., thioaminals or dithioacetals, respective...

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Bibliographic Details
Main Authors: Grzegorz Mlostoń, Małgorzata Celeda, Marcin Palusiak, Heinz Heimgartner, Marta Denel-Bobrowska, Agnieszka B. Olejniczak
Format: Article
Language:English
Published: Beilstein-Institut 2025-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
2,5-dihydro-1,3,4-thiadiazoles
enolizable 5-mercapto-1h-tetrazoles
insertion reactions
thiiranes
thiocarbonyl ylides
x-ray analysis
Online Access:https://doi.org/10.3762/bjoc.21.113
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https://doi.org/10.3762/bjoc.21.113

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