SIMPLE NEW ROUTES TO OXIMINOPHOSPHONODITHIOATES, 1,3,5,2-OXATHIAZAPHOSPHOLES AND 1,3,2-THIAZAPHOSPHOLINES FROM OXIMES AND THEIR DERIVATIVES

Abstract

2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, 1, reacted with ketoximes at 25° followed by alkylation with methyl iodide to give oximino-4-methoxyphenyl-S-methyl-phosphonodi-thoate, 4. p-Tolualdehyde oxime when treated with 1 gave 2,4,6-tri-p-tolyl-1,3,5-trithiolidine, 6. The reaction of benzohydroxamoyl chlorides with 1 yielded 1,3,5,2-oxathiazaphospholes, 8, whereas p-nitrobenzohydroxamoyl chloride gave 3,6-di(4-nitrophenyl)-1,4,2,5-dioxadiazine, 11. Diarylketoximes with 1 produced 13 and 14. 9-Benzanthrone oxime with 1 afforded 9-benzanthrone thione, 16. The reaction of oximes of phenyl phenylmethylketoximes or 1,3-diphenyl-2-propanone with 1 at 80° afforded 1,3,2-thiazaphospholines, 18.