Busch, Brett B. published the artcileThe Boron-Catalyzed Polymerization of Dimethylsulfoxonium Methylide. A Living Polymethylene Synthesis, Computed Properties of 5034-06-0, the publication is Journal of the American Chemical Society (2002), 124(14), 3636-3646, database is CAplus and MEDLINE.
Trialkyl and aryl organoboranes catalyze the polymerization of dimethylsulfoxonium methylide (1). The product of the polymerization is a tris-polymethylene organoborane. Oxidation affords linear telechelic α-hydroxy polymethylene. The polymer mol. weight was found to be directly proportional to the stoichiometric ratio of ylide/borane, and polydispersities as low as 1.01-1.03 have been realized. Although oligomeric polymethylene has been the most frequent synthetic target of this method, polymeric star organoboranes with mol. weights of 1.5 million have been produced. The average turnover frequency at 120° in 1,2,4,5-tetrachlorobenzene/toluene is estimated at >6 × 106 g of polymethylene (mol boron)-1 h-1. The mechanism of the polyhomologation reaction involves initial formation of a zwitterionic organoborane-ylide complex which breaks down in a rate-limiting 1,2-alkyl group migration with concomitant expulsion of a mol. of DMSO. The reaction was found to be first order in the borane catalyst and zero order in ylide. DMSO does not interfere with the reaction. The temperature dependence of the reaction rate yielded the following activation energy parameters (toluene, ΔH⧧ = 23.2 kcal/mol, ΔS⧧ = 12.6 cal deg/mol, ΔG⧧ = 19.5 kcal/mol; THF, ΔH⧧ = 26.5 kcal/mol, ΔS⧧ = 21.5 cal deg/mol, ΔG⧧ = 20.1 kcal/mol).
Journal of the American Chemical Society published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Computed Properties of 5034-06-0.
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