5925-57-5Relevant academic research and scientific papers
Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: Rhodium-catalyzed double C-H activation controlled by different directing groups
Zhang, Xi-Sha,Zhang, Yun-Fei,Li, Zhao-Wei,Luo, Fei-Xian,Shi, Zhang-Jie
supporting information, p. 5478 - 5482 (2015/04/27)
A rhodium(III)-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (C-H, C-S, O-H) and the formation of two bonds (C-C, C-O). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double C-H activation, the first of such examples in cross-oxidative coupling.
Azetidine derivatives, their preparation and medicaments containing them
-
, (2008/06/13)
The invention concerns compounds of formula (1) wherein: R represents a chain (A) or (B); R1 is methyl or ethyl; R2 is either an optionally substituted aromatic or an optionally substituted heteroaromatic ring; R3 and R4, identical or different, are either an optionally substituted aromatic or an optionally substituted heteroaromatic ring; R′ represents a hydrogen atom or a —CO—alk radical, their optical isomers, their salts, their preparation and medicines containing them.
BIOTRANSFORMATION OF ORGANIC SULFIDES. PART 6. FORMATION OF CHIRAL para-SUBSTITUTED BENZYL METHYL SULFOXIDES BY HELMINTHOSPORIUM SPECIES NRRL 4671
Holland, Herbert L.,Brown, Frances M.,Larsen, Brett G.
, p. 1561 - 1568 (2007/10/02)
The fungus Helminthosporium species NRRL 4671 has been used for the biotransformation of a series of para-substituted benzyl sulfides with substituent groups consisting of trifluoromethyl, halo, hydroxy, methoxy, acetoxy, nitro, cyano, amino, acetamido, acyl and carboxylic acid units.In all cases, sulfoxide formation occurred in good yoeld and with predominant (S) chirality at the sulfur position.A minor amount of sulfone product was also obtained from the halo- and methoxy-substituted substrates.
Superelectrophilic methylthiomethylation of aromatics with chloromethyl methyl sulfide/aluminum chloride (MeSCH2Cl:2 AlCl3) reagent
Olah,Wang,Neyer
, p. 276 - 278 (2007/10/02)
Effective methylthiomethylation of aromatics was achieved by using chloromethyl methyl sulfide/aluminum chloride (MeSCH2Cl:2 AlCl3) as the alkylating agent. Excess aluminum chloride activates the thiocarboxonium ion intermediate by coordinating with sulfur and thus diminishes back donation of 'electron density' into the carbocationic center, rendering it a superelectrophilic methylthiomethylating agent.
Reduction of Sulfoxides with Sodium or Benzyl Bromide
Bernard, Angela M.,Caredda, Maria G.,Piras, P. Paolo,Serra, Ermanno
, p. 329 - 330 (2007/10/02)
The reduction of dimethyl and diphenyl sulfoxides, and of alkyl and arylbenzyl sulfoxides to the corresponding sulfides can be carried out using sodium bromide without solvent or benzyl bromide in dimethylformamide, mostly through an oxidation-reduction cycle catalyzed by developing hydrobromic acid.
NOVEL AND EFFECTIVE METHODS FOR α-THIOALKYLATION OF AROMATIC COMPOUNDS
Torisawa, Yasuhiro,Satoh, Atsushi,Ikegami, Shiro
, p. 1729 - 1732 (2007/10/02)
Convenient and effective methods for the introduction of a methylthiomethyl group and other α-thioalkyl group into aromatic compounds are described.
ALKYLATION OF AROMATIC COMPOUNDS WITH PUMMERER REARRANGEMENT INTERMEDIATES. APPLICATION TO THE PREPARATION OF METHYL-ARYL COMPOUNDS
Stamos, Ioannis K.
, p. 2787 - 2788 (2007/10/02)
Pummerer intermediates generated from dimethylsulfoxide reacted with aromatic compounds in the presence of tin(IV) chloride to give methylthiomethylaryl products which were in turn desulfurized to methylaryl compounds with Raney-Ni.
Nucleophilic Substitution on 4-Methylbenzyl Thiocyanate with Nucleophiles
Oae, Shigeru,Yamada, Norihiro,Fujimori, Ken,Kikuchi, Osamu
, p. 248 - 256 (2007/10/02)
The reactions of 4-methylbenzyl thiocyanate (1) with several nucleophiles have been investigated.Compound 1 possesses three electrophilic sites, i.e., benzylic carbon, sulfur and cyano carbon, to receive nucleophilic attack.PhS- and CN- which have HOMO's of high energy levels appear to attack preferentially the sulfur atom.MeO- was found to attack preferably the cyanide carbon, while amines which have HOMO's of low energy levels prefer benzylic carbon to attack.The nucleophilic substitution on the sulfur or the cyanide carbon generates CN- or p-xylene-α-thiolate anion, strong nucleophiles, as the primary products, which then initiate the complex secondary reactions.The selective reactivities of three attacking sites for nucleophiles in 1 have been rationalized in terms of MO theory.
