Premium
A rare case of three rearrangements during the cycloaddition‐elimination reaction of 4‐methyl‐5‐phenylimino‐Δ 2 ‐1,2,3,4‐thiatriazoline with 2‐pyridyl isothiocyanate
Author(s) -
L'abbé Gerrit,
Allewaert Kathy,
Toppet Suzanne
Publication year - 1988
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.5570250539
Subject(s) - chemistry , cycloaddition , isothiocyanate , electrophile , ring (chemistry) , nuclear magnetic resonance spectroscopy , medicinal chemistry , phenyl isothiocyanate , reaction mechanism , stereochemistry , organic chemistry , catalysis
2‐Pyridyl isothiocyanate ( 7 ), with its electrophilic and basic properties, gives a series of ring‐transformation reactions with 4‐methyl‐5‐phenylimino‐1,2,3,4‐thiatriazoline ( 1 ) at 60°. 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 13 C nmr spectroscopy.