STUDIES ON ORGANOPHOSPHORUS COMPOUNDS-XXXVII SYNTHESES OF Δ5-1,2,3-DIAZAPHOSPHOLINES AND INDOLES FROM HYDRAZONES

Article abstract of DOI:10.1016/S0040-4020(01)98970-7

2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 1, reacts with phenylhydrazones of methylketones to give Δ⁵-1,2,3-daizaphospholines, 3; in one case 2-methyl-3-phenylindole, 4, was also isolated.Phenylhydrazones of cyclopentanone and cyclohexanone similarly yield the corresponding annulated P-heterocycles, 6a, 6b and as byproducts the indoles 7a and 7b, respectively.The sole product from the reaction of 1 with the phenylhydrazone of 1,3-diphenyl-2-propanone is 2-benzyl-3-phenylindole, 9.A mechanism for the formation of the diazaphospholines is suggested.