ADDITION REACTIONS OF PYRIDINIUM-AND RELATED N-YLIDES WITH 1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDES

Abstract

Pyridinium phenacylides react with 2,4-Bis-(4-Methoxyphenyl)-l,3,2,4-dithiadiphosphetane-2,4-disulfide 1a to give a mixture of 1,4,2-thiazaphosphole derivatives 8a-c and 1,3,2-oxathiaphosphole derivatives 9a-c in the ratio 2:1, respectively; while with compounds 1b-d give only 1,4,2-thiazaphosphole derivatives 13a-c. Compounds 12a-d are obtained from the reaction of compounds 9a-c with the corresponding alcohol. In the same way compounds 14 and 15 are produced from the reaction quinolinium- and iso-quinolinium phenacylides with 1a respectively. Mechanistic considerations on the formation of the products are discussed.