188445-80-9Relevant academic research and scientific papers
α-Phosphoryl sulfoxides. XI. Sulfenylation of α-phosphoryl sulfoxides and a general synthesis of optically active ketene dithioacetal mono-S-oxides
Mikolajczyk, Marian,Midura, Wanda H.,Wladislaw, Blanka,Biaggio, Francisco C.,Marzorati, Liliana,Wieczorek, Michal W.,Blaszczyk, Jaroslaw
, p. 2959 - 2972 (1997)
Sulfenylation and selenenylation of α-phosphoryl sulfoxides 1 with S-methyl methanethiosulfonate and phenylselenenyl bromide, respectively, affording α-methylsulfenyl- and α-phenylselenenyl-α-phosphoryl sulfoxides 8 and 9 are described. Sulfenylation of (+)-(S)- dimethoxyphosphorylmethyl p-tolyl sulfoxide 2 gave a mixture of optically active diastereoisomers of the sulfoxide 8a which is a key substrate in the Horner-Wittig synthesis of enantiomeric ketene dithioacetal mono-S-oxides 10. The E/Z ratio of geometrical isomers of 10 was determined and briefly discussed. The crystal and molecular structure of E-1-p-tolylsulfinyl- 1-methylsulfenyl-2-phenyl-ethene 10a is reported.
