585532-74-7Relevant academic research and scientific papers
One-pot oxidative conjugate hydrothiocyanation-hydrosulfenylation of Baylis-Hillman alcohols promoted by a protic ionic liquid
Yadav, Lal Dhar Singh,Patel, Rajesh,Srivastava, Vishnu Prabhakar
experimental part, p. 1789 - 1792 (2009/04/07)
The first example of one-pot oxidative conjugate hydrothiocyanation- hydrosulfenylation of acrylic ester derived Baylis-Hillman alcohols, that is, methyl 3-aryl-3-hydroxy-2-methylene-propanoate, is reported. The reaction involves protic ionic liquid [Hmim]HSO4-mediated oxidation of Baylis-Hillman alcohols with NaNO3 to give methyl (E)-α-formylcinnamates followed by conjugate addition of sulfur-centered nucleophiles (NH4SCN/PhSH) to afford the corresponding methyl β-thiocyanato (or β-phenylsulfenyl)-α-formylhydrocinnamates diastereoselectively in 74-87% yields in a one-pot procedure. After isolation of the product, the ionic liquid [Hmim]HSO4 could be easily recycled for further use without any loss of efficiency. Georg Thieme Verlag Stuttgart.
Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes
Kinoshita, Sayaka,Kinoshita, Hironori,Iwamura, Tatsunori,Watanabe, Shin-ichi,Kataoka, Tadashi
, p. 1496 - 1502 (2007/10/03)
Reactions of but-3-yn-2-one (2) with aldehydes 1 in the presence of a Lewis acid and dimethyl sulfide (3a) predominantly gave (E)-α-(halomethylene)aldols 4-5 in high yields, while reactions of methyl propiolate (6a) mainly afforded (Z)-3-halogeno-2-(hydro
