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A Rare Case of Three Rearrangements During the Cycloaddition-Elimination Reaction of 4-Methyl-5-phenylimino-Δ2-1,2,3,4-Thiatriazoline with 2-Pyridyl Isothiocyanate
L'abbe, Gerrit,Allewaert, Kathy,Toppet, Suzanne
, p. 1459 - 1462 (2007/10/02)
2-Pyridyl isothiocyanate (7), with its electrophillic and basic properties, gives a series of ring-transformation reactions with 4-methyl-5-phenylimino-1,2,3,4-thiatriazoline (1) at 60 deg C.Two dithiazolidines, 8 and 10, are formed as major products at an early stage of the reaction, whereas two thiadiazolidines, 9 and 11, predominate at the end.The mechanism (Schemes II and III) has been elucidated by following the reaction course under a variety of conditions and by analyzing the products by 13C nmr spectroscopy.
