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Addition‐rearrangement reactions of 5‐amino‐3‐oxo‐Δ 4 –1,2,4‐thiadiazolines
Author(s) -
L'Abbé Gerrit,
Albrecht Ernestine
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290226
Subject(s) - chemistry , hypervalent molecule , acetonitrile , electrophile , carbon disulfide , medicinal chemistry , sulfur , chloroform , sulfoxide , organic chemistry , photochemistry , catalysis , iodine
Abstract Bond‐switching rearrangement via hypervalent sulfur occurs during the reactions of 5‐anilino‐2‐benzyl‐3‐oxo‐Δ 4 –1,2,4‐thiadiazoline 5 with electrophilic nitriles, isothiocyanates, carbon disulfide and ketenes, yielding the products 6 and 7. In contrast, N,N' ‐ditolylcarbodiimide reacts with 5 to give the normal addition product 8 , which rearranges only partially to 9 in several solvents (chloroform, acetonitrile and dimethyl sulfoxide). The equilibrium position depends on the temperature, favoring 9 at higher temperatures.