CYCLOADDITION REACTIONS OF 1,3-DIPHENYLTHIAZOLOBENZIMIDAZOLE WITH FULVENE AND TROPONE SYSTEMS

Article abstract of DOI:10.1246/cl.1981.213

1,3-Diphenylthiazolo<3,4-a>benzimidazole (1) containing tetravalent sulfur reacts as a thiocarbonyl ylide dipole with 6,6-diphenylfulvene to give a mixture of two regioisomeric exo-<4 + 2> adducts and endo-<4 + 2>adduct.The reaction of 1 with tropone and 8,8-dicyanoheptafulvene proceeds via a <4 + 2> cycloaddition to the C4-C5 and C1-C2 bond of the addend to afford the exo-adduct and desulfurized compound respectively.