198211-40-4

Upstream product

• 97106-56-4 vinylidenebis(diphenylphosphine) disulfide 

Downstream Products

• 198211-45-9 [Au(C₆F₅)2(C(CH₂CH(COCH₃)2)(P(S)(C₆H₅)2)2)] 
• 198211-52-8 [Au(C₆F₅)2(C(CH₂OC₂H₅)(P(S)(C₆H₅)2)2)] 
• 198211-47-1 [Au(C₆F₅)2(C(CH₂CN)(P(S)(C₆H₅)2)2)] 

Relevant academic research and scientific papers

Synthesis of highly stable intermediates in Michael-type additions to the double bond in (SPPh2)2C=CH2

Treatment of vinylidenebis(diphenylphosphine) with elemental sulfur under reflux led to vinylidenebis(diphenylphosphine) disulfide, (SPPh2)2C=CH2, in good yields. Its co-ordination to a gold(III) centre activates the carbon-carbon double bond. Thus, the chelate complex [Au(C6F5)2{(SPPh2) 2C=CH2}]ClO4 reacted rapidly with carbon- or oxygen-donor nucleophiles (Nu-), such as acac- (acetylacetonate), CN-, C5H5- or OEt-, forming methanide-type derivatives [Au(C6F5)2{(SPPh2) 2CCH2Nu}]. These products can be considered as intermediates in Michael-type additions of HNu to the C=C bond, which in this particular case display high stabilities, allowing their isolation as solids. The crystal structure of the cyclopentadienyl derivative has been established by X-ray crystallography and displays a square-planar gold(III) centre with a cis disposition of the pentafluorophenyl groups and sulfur atoms of the chelating ligand, and sp2 hybridization of the endocyclic carbon atom with partial P-C double-bond character.