52117-57-4Relevant academic research and scientific papers
Solvent-enabled radical selectivities: Controlled syntheses of sulfoxides and sulfides
Wang, Huamin,Lu, Qingquan,Qian, Chaohang,Liu, Chao,Liu, Wei,Chen, Kai,Lei, Aiwen
supporting information, p. 1094 - 1097 (2016/01/20)
Controlling selectivity is of central importance to radical chemistry. However, the highly reactive and unstable radical intermediates make this task especially challenging. Herein, a strategy for taming radical redox reactions has been developed, in which solvent-bonding can alter the reactivity of the generated radical intermediates and thereby drastically alter the reaction selectivity at room temperature. Various β-oxy sulfoxides and β-hydroxy sulfides can be facilely obtained, some of which are difficult to synthesize by existing methods. Notably, neither a metal catalyst nor any further additives are necessary in these processes. Solvent selection alters the reactivity of the generated reaction intermediate and drastically switches the reaction selectivity under simple and mild conditions. Various β-oxy sulfoxides and β-hydroxy sulfides could be facilely obtained from readily available starting materials. Importantly, neither a metal catalyst nor an additional additive was necessary in these transformations.
Substituent Effect on the Enantioface-Differentiating Reaction of (R)- with m- or p-Substituted Acetophenones
Kunieda, Norio,Nokami, Junzo,Kinoshita, Masayoshi
, p. 526 - 529 (2007/10/02)
When lithiomethyl p-tolyl sulfoxide derived from (R)-(+)- was allowed to react with acetophenones which have a variety of m- or p-substituents, the corresponding diastereomeric mixture of β-hydroxy sulfoxides (RSSC and RSRC) was produced.The degree of enantioselectivity was affected by the nature of the substituent on benzene ring.The logarithms of RSSC/RSRC values thus obtained gave a good correlation with Hammett's ? values, affording a negative straight line.The results have been discussed in view of the stereochemical course of the reaction.
Diastereofacial Control in the Reaction of (R)-α-(p-Tolylsulfinyl)acetophenones with Several Organometallics
Fujisawa, Tamotsu,Fujimura, Atsushi,Ukaji, Yutaka
, p. 1541 - 1544 (2007/10/02)
The diastereofacial controlled addition of organometallics to optically active β-ketosulfoxide was achieved to furnish both diastereomers of β-hydroxy sulfoxide depending on the selection of organometallic reagents.Trichloromethyltitanium added to (R)-α-(
