61124-57-0Relevant academic research and scientific papers
Copper(I)-catalyzed addition of grignard reagents to in situ-derived N -sulfonyl azoalkenes: An umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers
Hatcher, John M.,Coltart, Don M.
supporting information; experimental part, p. 4546 - 4547 (2010/06/13)
The α-alkylation of N-sulfonyl hydrazones via in situ-derived azoalkenes provides an umpolung approach to ketone α-alkylation that has considerable potential with regard to catalysis and the direct incorporation of functionality not amenable to the use of enolate chemistry. Herein, we describe the first Cu(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes. This method is remarkable in its ability to deliver highly sterically hindered compounds that would be difficult or impossible to synthesize via traditional enolate chemistry, including those having up to three contiguous quaternary centers.
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.
