Methylsulfonyl chloride

The intermediacy of zwitterionic species was proposed for the addition of phenylsulfenyl chloride to dimethylaminomethyl-substituted enamines (465,466). They receive support from the observed lack of stereospecific addition of methylsulfonyl chloride to cw-morpholinopropene (although the trans enamine gives only one adduct) (466). 

Unambiguous evidence was provided for a relatively long-lived electron adduct to methylsulfonyl chloride formed in reaction (47) k J = (3.3 0.3) X 10 ° M s and involving pulse radiolytically generated hydrated electron ... 

Evans, M E, Long, L, Parrish, F W, Reaction of carbohydrates with methylsulfonyl chloride in NJSl-dimethylformamide. Preparation of some methyl 6-chloro-6-deoxyglycosides, J. Org. Chem., 33, 1074-1076, 1968. 

In a second German patent (70GEP1935272) (Scheme 28) the preparation of 5-methylsulfonyl-aminopyrazol-3-one 99 took place simply by reacting 5-amino-l,2-dihydropyrazol-3-one 98 with methylsulfonyl chloride at room temperature. 

An acetonide is used as a protecting group in the synthesis of a corticoid that incorporates no fewer than four halogen atoms. The sequence starts with the conversion of the terminal hydroxyl on the side chain at C21 to a better leaving group, a mesylate, by means of methylsulfonyl chloride (30-2) (Scheme 7.30). Treatment of that intermediate with lithium chloride displaces the mesylate to afford the 21-chloro analogue (30-3). Addition of chlorine then leads to the 9a,l l)8-dichloro derivative (30-4). 

METHYLSULFONYL CHLORIDE (124-63-0) Combustible liquid (flash point >212°F/> 100°C). Reacts with water, acid, or acid fumes, forming hydrochloric acid. Violent reaction with ammonia, caustics, strong oxidizers. Aqueous solution incompatible with sulfuric acid, ammonia, aliphatic amines, alkanolamines, bases, isocyanates, alkylene oxides, epichlorohydrin Attacks metals in the presence of moisture. 

AI3-52234 Chloromethyl sulfone EINECS 204-706-1 HSDB 5605 Mesyl chloride Methanesulfonic acid chloride Methanesulfonyl chloride Methanesulfuryl chloride Methanesulphonyl chloride Methyl sulfochloride Methylsulfonyl chloride NSC 16039 UN3246. Liquid bp = 162, bpii = 55 d = 1.4805 insoluble in H2O, soluble in EtOH, EtzO. 

Synonyms Chloromethyl sulfone Mesyl chloride Methylsulfonyl chloride MSC... 

Manuf./Distrib. Sumitomo Seika Methylsulfonyl chloride. See Methanesulfonyl... 

The evidence for the formation of the sulfene intermediate, probably via a concerted E2 type elimination reaction, has been reviewed by King and Rathore. For instance, when the reaction shown in Equation 11 was performed using deuterated isopropanol (MczCHOD), the monodeuterated isopropyl sulfonate 10 was obtained (90% yield). The presence of a fi ee sulfene intermediate was also indicated by mass spectral evidence in the reaction of ethylsulfonyl chloride with deuterated methanol (MeOD) in the presence of 3-methylpyridine. Further evidence for sulfene formation derived from kinetic studies of the reaction of methylsulfonyl chloride with isopropanol in the presence of triethylamine. The... 

Kinetic and deuteration experiments demonstrated that the hydrolysis of (tri-methylsilyl) methylsulfonyl chloride 14 in water (0.01 MKCl) involves the sulfenes 15 and 16 " (Equation 13). 

The methylsulfonylation of toluene by reaction with methylsulfonyl chloride in the presence of aluminium chloride catalyst affords methyl tolyl sulfone (52% yield) with an ortho meta para isomer ratio of 53 14 33. Attempts have been made to obtain greater selectivity in sulfonylations a supported Lewis acid catalyst has been recommended for selective sulfonylation, but it did not give good results in the methylsulfonylation of toluene. The best pura-selectivity... 

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