7334-52-3Relevant academic research and scientific papers
Neighboring-Group Participation in the Gas Phase. Loss of Benzaldehyde from dialkylsilyl-Substituted 1,3-Dithianes
Faessler, Juerg,Huber, Priska,Bratovanov, Svetoslav,Bigler, Laurent,Bild, Norbert,Bienz, Stefan
, p. 1855 - 1862 (1995)
dialkylsilyl-substituted 1,3-dithianes show in CI-MS an abundant loss of benzaldehyde from the (1+) quasi-molecular ion.The fragmentation is explained with an intramolecular redox process, where a hydride is proposed to be transfer
Cyanuric chloride-catalyzed thioacetalization for organocatalytic synthesis of thioacetals
Liu, Yaqin
, p. 679 - 682 (2016/05/09)
The thioacetalization of aromatic aldehydes has been realized with broad diversity in the presence of various thiols and thiophenols using cyanuric chloride as an organocatalyst.
Ethyl lactate mediated thioacetalization of aldehydes at ambient temperature
Wan, Jie-Ping,Jing, Yanfeng,Liu, Yunyun
, p. 1302 - 1305 (2016/09/28)
Dithioacetalization reactions of aldehydes with thiols/thiophenols have been successfully achieved at room temperature by employing the green, bio-based ethyl lactate as the reaction medium. By means of this sustainable approach, a class of dithioacetals has been acquired with high diversity and efficiency.
INTRODUCTION OF ALKYL SUBSTITUENTS TO AROMATIC COMPOUNDS
-
Page/Page column 67, (2016/09/15)
Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.
Reductive Alkylation of Arenes by a Thiol-Based Multicomponent Reaction
Parnes, Regev,Pappo, Doron
supporting information, p. 2924 - 2927 (2015/06/30)
A simple and highly chemo- and regioselective method for introducing primary alkyl substituents into aromatic compounds was developed. The method is based on an electrophilic aromatic substitution of an aldehyde, promoted by a thiol, to afford 1-(alkylthio)alkylarenes, which can either be reduced in situ with triethylsilane or reacted further. This multicomponent reaction enables the direct introduction of both aromatic and linear and branched aliphatic alkyl groups into arenes. The above one-pot protocol may be performed in air and in the presence of water and is compatible with various functional groups.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
Synthesis in ionic liquids only: Access to α-oxo-γ-thio-esters via Mukaiyama coupling
Jebri, Khouloud,Mazières, Marie-Rose,Ballereau, Stéphanie,Ben Ayed, Ta?cir,Plaquevent, Jean-Christophe,Baltas, Michel,Guillen, Frédéric
supporting information, p. 1353 - 1356 (2014/03/21)
Ionic liquids are solvents general enough to conduct a multi-step process in organic synthesis. We show that both the preparation of starting materials (thioacetals and enoxysilane) as well as their coupling can be realized in such medium.
Chemoselective and odorless transthioacetalization of acetals using α-oxo-ketene dithioacetals as thiol equivalents
Yu, Hai-Feng
, p. 1280 - 1286 (2013/04/10)
Using α-oxo-ketene dithioacetals 1a as odorless thiol equivlents, an efficient and odorless transthioacetalization of acetals 2 has been developed. In the presence of MeCOCl in MeOH, the cleavage of 1a commences to generate thiols at both room and reflux temperatures, and the generated thiols then react with acetals 2 to give correspecting thioacetals 3 in good yield. This transthioacetalization is characterized by mild reaction conditions, simple procedure, good yields, and perfect chemoselectivity. It is noteworthy that only a very faint odor of thiols can be perceived during both the reaction and workup.
Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles
Gellert, Beate A.,Kahlcke, Nils,Feurer, Markus,Roth, Stefanie
supporting information; experimental part, p. 12203 - 12209 (2011/11/07)
Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.
Silica-supported phosphorus pentoxide: A reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions
Shaterian, Hamid Reza,Azizi, Kobra,Fahimi, Nafiseh
experimental part, p. 85 - 91 (2012/01/06)
Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free an
