16096-71-2

Upstream product

• 52190-35-9 2-(methylthio)cyclohexanone 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 124-63-0 methanesulfonyl chloride 
• 1056477-06-5 2-bromocyclohexanone 
• 822-87-7 2-Chlorocyclohexanone 
• 25542-62-5 6-bromo-hexanoic acid ethyl ester 

Downstream Products

• 89730-08-5 2-(Nonylsulfonyl)cyclohexanon 
• 89729-99-7 2-(Hexylsulfonyl)-1-cyclohexanon 
• 108920-21-4 trans-2-(methylsulfonyl)cyclohexanol 
• 108920-20-3 cis-2-(methylsulfonyl)cyclohexanol 
• 89730-00-7 2-(2-Phenylethylsulfonyl)-1-cyclohexanon 
• 85058-04-4 2-(Propylsulfonyl)-1-cyclohexanon 
• 89730-09-6 2-(3-Butenylsulfonyl)-1-cyclohexanon 

Relevant academic research and scientific papers

Mechanisms of Hydrolysis of (Trimethylsilyl)methanesulfonyl Chloride. Sulfene-Enamine Reactions in Water

Kinetic, product analysis, and deuteration experiments are consistent with the following mechanisms of hydrolysis of (trimethylsilyl)methanesulfonyl chloride (1) (in 0.01 M KCl at 1 deg C): (a) pH /= 10.0, attack of hydroxide anion (i) at silicon to yield sulfene (5) and (ii) at an α-hydrogen to form (trimethylsilyl)sulfene (4), in each case followed by trapping of the sulfene to give either methanesulfonate (3) or (trimethylsilyl)methanesulfonate (6) salts.Aqueous potassium fluoride catalyzes the hydrolysis of 1 with formation of the methanesulfonate 3, evidently by way of silicophilic attack of fluoride anion on 1 with formation of sulfene (5).Reaction of 1 with an enamine 7 in water (at pH 8 or 9), with or without fluoride, gives two characteristic sulfene-enamine products, (i) the four-membered cycloadduct 8 and (ii) the methylsulfonyl aldehyde 9.The same or related products are also obtained from methanesulfonyl, 2-propanesulfonyl, and phenylmethanesulfonyl chlorides and enamines in water (at pH 9).Hydrolysis of 1 is also catalyzed by aniline or triethylamine evidently giving 5.

Studies on the Stereoselectivity of Hydride Reductions on 2-(Methylthio)- and 2-(Methylsulfonyl)cyclohexanones

The results obtained in the reductions of 2-X-cyclohexanones and cis- and trans-4-tert-butyl-2-X-cyclohexanones (X=SMe, SO2Me) with different hydrides are reported.When the sulfur functions adopt the axial disposition, the cyclohexanol resulting from the

New Synthetic Methods, 10. - β-Ketosulfones, Useful Ethylenediide Equivalents: The Synthesis of Unsaturated Carboxylic Acids

α-Alkyl-thiolated cycloalkanones are, after oxidation to sulfones, ring-opened by halogenation to yield α-halosulfones.Ramberg-Baecklund rearrangement forms unsaturated carboxylic acids.The position of the newly formed double bond is fixed by the ring siz