Campbell, Stewart John et al. published their research in Canadian Journal of Chemistry in 1976 |CAS: 58966-31-7

The Article related to asym sommelet rearrangement benzylsulfonium, sulfonium asym sommelet rearrangement, Physical Organic Chemistry: Rearrangements, Including Isomerization and Tautomerization and other aspects.Synthetic Route of 58966-31-7

Campbell, Stewart John; Darwish, David published an article in 1976, the title of the article was Asymmetric induction in the Sommelet rearrangement of chiral benzylsulfonium salts.Synthetic Route of 58966-31-7 And the article contains the following content:

The Sommelet rearrangement of (+)-ethylmethyl-p-nitrobenzylsulfonium perchlorate (I) and (+)-ethylmethyl-p-chlorobenzylsulfonium perchlorate (II) are described. Elution of I through a hydroxide exchange resin generated ethylmethylsulfonium p-nitrobenzylide [(+)-III] which decomposed in methanol at room temperature to Et 2-methyl-5-nitrobenzyl sulfide and (+)-Me α-(2-methyl-5-nitrophenyl)ethyl sulfide with 18 to 20.3% asymmetric induction. Decomposition of II in NaOMe solution at 70° produced Et 2-methyl-5-chlorobenzyl sulfide and (+)-Me α-(2-methyl-5-chlorophenyl)ethyl sulfide with 21 to 25.5% asymmetric induction. The lower estimates of asymmetric induction for each sulfide were made by comparison with sp. rotations of authentic samples obtained by synthesis and resolution The higher estimates were obtained by the use of a chiral lanthanide shift reagent Eu(hfbc)3 with the sulfone derivatives of these chiral sulfides. The ylide (+)-III reacted with aldehydes to produce oxiranes with no induction of asymmetry. The experimental process involved the reaction of 1-(5-Chloro-2-methylphenyl)ethanol(cas: 58966-31-7).Synthetic Route of 58966-31-7

The Article related to asym sommelet rearrangement benzylsulfonium, sulfonium asym sommelet rearrangement, Physical Organic Chemistry: Rearrangements, Including Isomerization and Tautomerization and other aspects.Synthetic Route of 58966-31-7

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