66164-48-5

Upstream product

• 51207-25-1 ethylphenylsulfoxide 
• 1079-66-9 chloro-diphenylphosphine 
• 31238-57-0 diphenyl(phenylthiomethyl)phosphine oxide 
• 74-88-4 methyl iodide 
• 882-33-7 diphenyldisulfane 
• 1733-57-9 ethydiphenylphosphine oxide 
• 84904-73-4 1-chloro-1-phenylthioethyl-diphenylphosphine oxide 
• 719-80-2 Ethyl diphenylphosphinite 
• 5535-49-9 2-Chloroethyl phenyl sulfide 

Downstream Products

• 84904-72-3 Diphenyl (1-phenylthiovinyl)phosphine oxide 
• 113107-95-2 1,2-dichloro-1-phenylthiophenyl phosphine oxide 
• 84904-74-5 1-phenylsulphinylethyldiphenylphosphine oxide 
• 84904-73-4 1-chloro-1-phenylthioethyl-diphenylphosphine oxide 
• 67150-82-7 (1'-(phenylthio)ethylidene)cyclohexane 
• 85894-88-8 3-ethyl-2-(phenylthio)-2-pentene 
• 85895-15-4 4-ethyl-3-(phenylthio)-3-hexene 
• 85895-62-1 1-bromo-2-(phenylthio)-3-ethylpent-2-ene 
• 85895-14-3 (1'-(phenylthio)propylidene)cyclohexane 
• 85895-49-4 <1-(phenylthio)-2-bromoethylidene>cyclohexane 
• 85895-18-7 C₂₂H₂₇NO₂S₂ 
• 85895-01-8 (3,3-bis(phenylsulfonyl)-1-(phenylthio)propylidene)cyclohexane 
• 61173-97-5 1-phenylthiopropyldiphenylphosphine oxide 
• 84904-77-8 2-methyl-4-phenylthiohex-3-ene 

Relevant academic research and scientific papers

Stereoselective syntheses of 1,2-dialkyl-1-phenyl cyclopentanes involving intramolecular carbolithiation of α-thioalkenes

2-Ethyl-1-methyl-1-phenyl cyclopentane, unavailable by butyllithium-promoted carbocyclisation of the corresponding alkenyl selenide, has been synthesized from 6-methylseleno-6-phenyl-1-phenylthio-1-heptene and 7-methylseleno-7-phenyl-2-phenylthio-2-octene with high stereocontrol at all the three stereogenic centers. Depending upon the solvent used, the derivative in which the methyl- and the phenylthiomethyl groups are cis (in THF) or trans (in pentane) to each other are formed selectively.

A THREE COMPONENT KETONE SYNTHESIS FROM A PHENYLTHIOVINYLPHOSPHINE OXIDE

The anion formed by addition of an alkyl-lithium to the vinyl phosphine oxide (4) reacts with aldehydes to give vinyl sulphides, easily hydrolysed to ketones.

Thiol Esters from Sulfoxides via Rearrangement of Sulfoxide Phosphines to Sulfide Phosphine Oxides

Treatment of α-lithio sulfoxides with (1) ClP-(C6H5)2 and (2) I2 (isolate sulfide phosphine oxide 3) followed by (3) C4H9Li and (4) O2 affords thiol esters.

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.