T. Kawashima et al., SYNTHESES, STRUCTURES, AND THERMOLYSES OF TETRACOORDINATE 1,2-LAMBDA(4)-OXATHIETANES, Phosphorus, sulfur and silicon and the related elements, 95-6(1-4), 1994, pp. 439-440
Title compounds were synthesized by oxidative cyclization of the corre
sponding dihydroxy sulfide with bromine in the presence of triethylami
ne. The X-ray crystallographic analysis of S-phenyl derivative shows t
hat it has a distorted trigonal bipyramidal structure. Thermolysis gav
e no olefin, but instead benzhydryl phenyl ketone, benzophenone, and t
he corresponding cyclic sulfenate and thioketal were formed. A trace o
f 2,2,3-triphenyloxirane was also formed. The mechanism is discussed.