SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE DETERMINATION OF 3,4-DIPHENYL-6-(DIPHENYLMETHYL)-1,5-DIOXA-2-THIANE-2-OXIDE

Erythro and threo-1,2-diphenyl-2-tert-butylsulfinylethanols 5 and 8 were prepared from the condensation of the alpha-lithio derivative of benzyl-tert-butyl sulfoxide with benzaldehyde. Reaction of 5 with sulfuryl chloride gave the title compound, (2R*,3S*,4R*,6R*)-3,4-diphenyl-6-(diphenylmethyl)-1,5-dioxa-2-th?? iane-2-oxide 6, the first representative of a new heterocyclic ring system. Similar treatment of 8 resulted in the formation of 7, a stereoisomer of 6. This same compound was also obtained by photolysis of 6. In both 6 and 7 the S = O bond is in axial orientation.