13033-58-4Relevant academic research and scientific papers
Diastereoselective synthesis of tetrahydrofurans from Aryl 3-chloropropylsulfoxides and aldehydes
Komsta, Zofia,Barbasiewicz, Michal,Makosza, Mieczyslaw
supporting information; experimental part, p. 3251 - 3259 (2010/08/19)
Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intramolecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has electron-donating groups.
α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms
Toyota, Akemi,Ono, Yoshinori,Chiba, Jun,Sugihara, Takumichi,Kaneko, Chikara
, p. 703 - 708 (2007/10/03)
Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.
Organic Disulfides and Related Substances. 43. Properties of a Mercaptoalkyl Sulfoxide, a Novel Class of Structure
Field, Lamar,Bowman, Gary T.
, p. 2771 - 2775 (2007/10/02)
3-Mercaptopropyl phenyl sulfoxide (4) was prepared by reaction of 3-chloropropyl phenyl sulfoxide (2) with sodium trithiocarbonate (3).The mercaptopropyl sulfoxide 4 could be obtained only in a maximum purity of 93percent (and yield of 75percent) because
