117531-22-3

Upstream product

• 84642-46-6 3-bromo-2-<(trimethylsilyl)methyl>propene 
• 13133-62-5 thiophenolate 
• 74532-54-0 3-trimethylsilyl-2-(methylsulphonyloxymethyl)prop-1-ene 
• 81302-80-9 2-(trimethylsilylmethyl)prop-2-en-1-ol 
• 116279-69-7 <2-<(phenylthio)methyl>allyl>trimethylsilane 

Downstream Products

• 158183-09-6 (Z)-5-(2-methoxy-2-phenethyl)-6-phenylthiohex-5-en-2-one 
• 117531-27-8 1,7-diphenyl-4-phenylthiomethyleneheptane-1,7-dione 
• 117531-26-7 1-phenyl-4-phenylsulfinylmethylpent-4-en-1-one 
• 117531-25-6 1-Phenyl-4-phenylsulfanylmethyl-pent-4-en-1-one 
• 117531-23-4 (Z)-2-(3-phenylthio-2-trimethylsilylmethylallyl)cyclohexanone 
• 117531-24-5 (Z)-1-phenyl-5-phenylthio-4-trimethylsilylmethylpent-4-en-1-one 

Relevant academic research and scientific papers

Allylation with Pummerer-generated Subtituted Vinylthionium Ions

Pummerer-derived substituted vinylthionium ions (allyl phenyl sulfoxide, TMSOTf, EtN(i-Pr)2, CH2Cl2, -78 deg C) with a β-trimethylsilylmethyl (2), γ-phenyl (14), or γ-phenylthio (15) group allylate the enol silyl ethers of acetophenone (3) and cyclohexanone (4) in good yield.Allylation with (14) and (15) required slow addition of base in order to limit the rate of production of intermediate, and thus avoid unwanted sila-Pummerer type products.Huenigs's base conjugate addition was not observed in these cases.Both the (E)- and (Z)- forms of allyl sulfoxide (15) were shown to equilibrate to the (E)-transoid conformer prior to allylation resulting in exclusive (E)-vinyl sulfide formation.Blocking of the γ-position resulted in preferential α-attack.

THE SCOPE OF A NEW MASKED MICHAEL REACTION INVOLVING A PUMMERER INTERMEDIATE

Huenig's base has been found to compete as a nucleophile in the alkylation of Pummerer generated vinylthionium ions.This discovery has been used in extending the scope of the novel masked Michael addition reaction.