18086-93-6Relevant academic research and scientific papers
Catalytic asymmetric addition of thiols to nitrosoalkenes leading to chiral non-racemic α-sulfenyl ketones
Hatcher, John M.,Kohler, Mark C.,Coltart, Don M.
supporting information; experimental part, p. 3810 - 3813 (2011/09/16)
The first asymmetric organocatalytic sulfenylation of in situ derived nitrosoalkenes leading to chiral nonracemic α-sulfenylated ketones is described. The transformation proceeds in an umpolung fashion, relative to enolate/azaenolate methods, and uses simple thiols, thereby obviating the need for electrophilic sulfur reagents.
Conversion of Tosylhydrazones of α-Halogeno-aldehydes and -ketones into the Corresponding Phenylthio- and Phenylseleno-derivatives
Reese, Colin B.,Sanders, H. Paul
, p. 2719 - 2724 (2007/10/02)
The tosylhydrazones of 2-chlorocyclohexanone, 2-chlorocyclopentanone, 1-chloropropanone, phenacyl chloride, 2-bromoheptanal and 2-bromo-2-methylpropanal (1), (5a),(7a),(8b), and (9b), respectively, reacted rapidly with thiophenol and an excess of triethylamine in tetrahydrofuran at -78 deg C to give the corresponding α-phenylthio-substituted tosylhydrazones (3a), (5b), (7b), (8c), and (9c) in good yields.The α-phenylseleno-substituted tosylhydrazones (3b),(5c), (6c), (8d), and (9d) were similarly prepared, in satisfactory yields, by treating the corresponding α-halogeno-substituted tosylhydrazones with benzeneselenol and an excess of triethylamine.Several α-phenylthio-substituted carbonyl compounds and 2-phenylselenocyclohexanone (4b) were regenerated from the corresponding tosylhydrazones in good yields.
