5925-82-6Relevant academic research and scientific papers
Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride
Cheng, Hong-Gang,Pu, Maoping,Kundu, Gourab,Schoenebeck, Franziska
supporting information, p. 331 - 334 (2019/12/30)
We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.
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.
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.
