119703-98-9

Upstream product

• 7205-91-6 phenylthiomethyl chloride 
• 19980-33-7 6-methyl-1-trimethylsiloxycyclohex-1-ene 
• 16467-05-3 2-Methyl-1-vinyl-cyclopentanol 
• 1120-72-5 2-Methylcyclopentanone 
• 127869-16-3 tert-Butyl-dimethyl-(2-methyl-1-vinyl-cyclopentyloxy)-silane 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 2816-57-1 2,6-dimethylcyclohexanone 

Relevant academic research and scientific papers

AN EPISULFONIUM ION MEDIATED RING EXPANSION OF 1-ALKENYLCYCLOALKANOLS

It has been found that TBDMS ethers of 1-alkenylcycloalkanols are readily rearranged to the ring expanded α-(1-phenylthioalkyl)cycloalkanones in high yields via episulfonoium ions.

α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION

For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.