106988-20-9Relevant academic research and scientific papers
Metal-free oxidative coupling of alkyl chlorides with thiols: An efficient access to sulfoxides
Liu, Qian,Zhao, Xiaoqian,Xu, Feng,Li, Gaoqiang
, (2020)
An efficient and step-economical access to sulfoxides from thiols and alkyl halides in the presence of I2O5 and DBU via direct oxidative couplings is described here. It is the first case that combined Williamson sulfide synthesis and subsequent sulfide oxidation into one step manipulation for sulfoxides preparation. This protocol features wide substrate scope, mild and metal-free conditons, the use of naturally abundant starting materials and avoidance of over-oxidation.
Method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by one-step reaction in metal free condition
-
Paragraph 0062; 0063; 0064; 0065, (2019/04/06)
The invention discloses a method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by a one-step reaction in a metal free condition. The method can be used for preparing aseries of sulfoxide compounds in a mild condition by taking benzyl chloride compound and thiophenol as reaction raw materials, iodine pentoxide as an oxidizing agent and 1,8-diazabicycloundecylenic-7-ene as alkali with a high yield. By taking halogenated hydrocarbon and thiol as reactants directly, compared with known and popular methods of generating thioether by halogenated hydrocarbon and thiolunder the action of strong alkali, separating a thioether compound and oxidizing the thioether to synthesize sulfoxide through an oxidizing agent, the reaction steps are shortened to one step from two steps. The middle treatment process of the reaction is few, the atom economy is good, and no transitional metal catalysts take part in the reaction, so that the synthetic cost is low, the reaction condition is mild, and the method opens up a novel and efficient path which is high in atom economy and low in cost for preparing the sulfoxide compounds and has a wide application prospect.
A combined theoretical and experimental investigation on the enantioselective oxidation of aryl benzyl sulfides in the presence of a chiral titanium catalyst
Naso, Francesco,Capozzi, Maria Annunziata M.,Bottoni, Andrea,Calvaresi, Matteo,Bertolasi, Valerio,Capitellil, Francesco,Cardellicchio, Cosimo
experimental part, p. 13417 - 13426 (2010/06/16)
An experimental investigation of the enantioselective oxidation of aryl benzyl sulfides by tert-butyl hydroperoxide in the presence of a titanium/hydrobenzoin catalyst has shown that these sulfides are ideal substrates for this catalytic system, with negl
Ring Expansion of Cyclobutanones to Cyclopentanones via α-Lithioalkyl Aryl Sulfoxides and Selenoxides
Gadwood, Robert C.,Mallick, Ishwar M.,DeWinter, Amy J.
, p. 774 - 782 (2007/10/02)
Reaction of α-lithioalkyl 2-chlorophenyl sulfoxides (prepared from the corresponding sulfoxides and LDA) with cyclobutanones affords adducts which undergo ring expansion to cyclopentanones upon treatment with potassium hydride.This reaction only works for cyclobutanones substituted at C2 with at least one phenyl or alkenyl group (type I and type II cyclobutanones).Cyclobutanones substituted at C2 with at least one alkyl group (type III and type IV cyclobutanones) undergo similar ring expansion upon treatment with α-lithioalkylphenyl selenoxides followed by direct thermolysis of the adducts.With both the sulfoxide and selenoxide reagents, the carbon atom inserted into the cyclobutanone can be unsubstituted, monosubstituted, or disubstituted.The ring expansions of 17 different cyclobutanones to 29 different cyclopentanones are presented.
