13119-15-8

Upstream product

• 17302-63-5 methanethiolate 
• 1806-49-1 diphenyl(chloromethyl)phosphine oxide 
• 719-80-2 Ethyl diphenylphosphinite 
• 542-81-4 sulfure de methyle et de 2-chloroethyle 
• 65567-06-8 lithium diphenylphosphide 
• 829-85-6 diphenylphosphane 
• 884-74-2 (diphenylphosphinoyl)methanol 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 13119-14-7 diphenylphosphino(methylthio)methane 

Downstream Products

• 123146-54-3 Acetic acid (diphenyl-phosphinoyl)-methylsulfanyl-methyl ester 
• 124666-22-4 (methylsulfinylmethyl)diphenylphosphane oxide 
• 123146-55-4 [(α-chloro)(methylthio)methyl]diphenylphosphine oxide 
• 66004-04-4 1-methylthioethyldiphenylphosphine oxide 
• 161957-22-8 [(α-chloro)sulfinylmethyl]diphenylphosphine oxide 
• 87762-89-8 2-(Diphenyl-phosphinoyl)-4,5-dimethyl-2-methylsulfanyl-3,6-dihydro-2H-thiopyran 1-oxide 
• 87762-74-1 (Diphenylphosphoryl)(methylthio)sulfine 
• 59625-05-7 C₁₄H₁₅O₃PS 

Relevant academic research and scientific papers

Optical resolution and the stereoelectronic properties of chelating (±)-[(methylsulfinyl)methyl]diphenylphosphine

Optical resolution of the asymmetric chelating agent (±)-Ph2PCH2S(O)Me has been achieved via fractional crystallization of a pair of diastereomeric palladium(II) cationic complexes containing the sulfinyl-substituted ligand and ortho-metallated (S)-[1-(dimethylamino)ethyl]naphthalene. The X-ray structural analysis of the perchlorate salt of the less-soluble diastereomer confirmed that the sulfinyl-substituted phosphine co-ordinated to the palladium via phosphorus and oxygen with the non-co-ordinated sulfur having an R absolute configuration. An unusual electronic repulsion is observed between palladium and the non-bonded sulfur lone pair thus directing the methyl substituent on sulfur to a sterically unfavored axial position. Furthermore, a two-dimensional rotating frame Overhauser enhancement 1H NMR study of the complex in CDCl3 confirmed that this intramolecular electronic interaction outweighs the general steric considerations in solution. Optically pure (R)-(+)-Ph2PCH2-S(O)Me was displaced from the resolving palladium complex with 1,2-bis(diphenylphosphino)ethane.

Stereoselective Horner-Wittig synthesis of (Z)-1-chlorovinyl sulfoxides

This paper describes the synthesis of (Z)-1-chlorovinyl sulfoxides 1 by the Horner-Wittig reaction. The required [(α-chloro)sulfinylmethyl]diphenylphosphine oxides 2 (R1=Me, c-Hex, Ph, p-Tol, p-(CF3)Ph), were prepared in high yields

A Horner-Wittig synthesis of 1-chlorovinyl sulfoxides

1-Chlorovinyl sulfoxides 1 were prepared by Horner-Wittig reaction of the readily accessible [(α-chloro)sulfinylmethyl)diphenylphosphine oxides 2 with aldehydes. Excellent Z-selectivity was observed in most cases.

Acyl anion equivalents: Synthesis of ketones and enones from α-phenylthioalkylphosphine oxides

The sulphenylated phosphine oxides Ph2P(O)·CH(SR2R1, easily prepared from triphenylphosphine, diphenyl or dimethyl disulphide, and an alkyl halide, form anions which act as acyl anion equivalents. Reaction with aldehydes and ketones gives vinyl sulphides, which can be hydrolysed to carbonyl compounds. Reaction with α-phenylthio-and α-methoxy-aldehydes and ketones gives enone precursors. The scope and limitations of the method are described.