STUDIES ON ORGANOPHOSPHORUS COMPOUNDS-XXXVI SIMPLE NEW ROUTES TO PHOSPHORINS FROM 2-HYDROXY-, 2-MERCAPTO-, AND 2-AMINOBENZOIC ACIDS AND THEIR DERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)98969-0

2-Hydroxybenzoic acid heated with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 1, gave 2-(p-methoxyphenyl)-4H-1,3,2-benzoxathiaphosphorin-4-one 2-sulfide, 3, and its thio analogue, 4, while its ethyl or phenyl esters gave 4 as the sole product. 2-Mercaptobenzoic acid and its ethyl ester when heated with 1 produced 3H-1,2-benzodithiole-3-one, 8, 3H-1,2-benzidithiole-3-thione, 9, and 2-(p-methoxyphenyl)-4H-1,3,2-benzodithia-phosphorin-4-one 2-sulfide, 10.The reaction of 2-aminobenzoic acid with 1 gave 1,2-dihydro-2-(p-methoxyphenyl)-4H-3,1,2-benzoxaphosphorin-4-one 2-sulfide, 12.Reactions of 1 with methyl 2-aminobenzoate and 2-aminobenzamides are described.Mechanistic considerations for the formation of the heterocyclic phosphorus compounds are presented.