Novel intramolecular cyclization reaction involving a thionitroso group: Formation of a 3,3a-dihydro-2,1-benzisothiazole from an o-alkylthionitrosoarene

Article abstract of DOI:10.1246/cl.1998.981

A thionitrosoarene generated by the desulfurization reaction of a stable N-thiosulfinylaniline bearing a bowl-type substituent underwent the intramolecular cyclization reaction involving the ortho-alkyl group to afford the corresponding 3,3a-dihydro-2,1-benzisothiazole. The intermediacy of the thionitrosoarene was corroborated by a trapping experiment with aniline.