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Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113
Graphical Abstract
Scheme 1: Typical [3 + 2] cycloaddition (above) and trapping (below) reactions of thiocarbonyl S-methanides 1a...
Scheme 2: Ambident reactivity of 5-mercapto-1H-tetrazoles 4 towards dimethyl 2-arylcyclopropane dicarboxylate...
Scheme 3: Regioselectivity of [3 + 2] cycloadditions of diazomethane with adamantanethione (7a) [22,24,25], and sterica...
Scheme 4: The in situ generation of sterically crowded thiocarbonyl S-methanides 1c,d (via a 1,3-dipolar cycl...
Scheme 5: Reactions of the in situ-generated thiocarbonyl S-methanides 1 (from 1,3,4-thiadiazolines 2) with e...
Figure 1: (a) Molecular structure of the N-insertion product (thioaminal) 9i. Atoms are represented by therma...
Scheme 6: Stepwise mechanism of the competitive N- and S-insertion reactions between the in situ-generated th...
Scheme 7: Mechanism of the isomerization of initially formed thioaminals 9 to dithioacetals 10.