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α-Phosphoryl sulfoxides. XI. Sulfenylation of α-phosphoryl sulfoxides and a general synthesis of optically active ketene dithioacetal mono-S-oxides

✍ Scribed by Marian Mikołajczyk; Wanda H. Midura; Blanka Wladislaw; Francisco C. Biaggio; Liliana Marzorati; MichałW. Wieczorek; Jarosław Błaszczyk

Book ID
104207516
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
624 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Sulfenylation and selenenylation of ~-phosphoryl sulfoxides I with S-methyl methanethiosulfonate and phenylselenenyl bromide, respectively, affording ~-methylsulfenyland ~-phenylselenenyl-ot-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 F~l-ptolylsulfinyl-1 -methylsulfenyl-2-phenyl-ethene 10a is reported

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α-phosphoryl sulfoxides. X. A general synthesis of optically active α-chlorovinyl sulfoxides
✍ Marian Mikołajczyk; Jerzy A. Krysiak; Wanda H. Midura; MichałW. Wieczorek; Jaros 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 439 KB

A general and efficient synthesis of enantiomeric c~-chlorovinyl p-tolyl sulfoxides 1 using (+)-(S)c(S)s-Ct-chloro-ct-dimethoxyphosphorylmethyl p-tolyl sulfoxide as a key substrate for the Horner-Wittig reaction with carbonyl compounds is described. The E/Z ratio of geometrical isomers of I was dete