40620-06-2Relevant academic research and scientific papers
An odorless thia-Michael addition using Bunte salts as thiol surrogates
Lin, Ya-Mei,Lu, Guo-Ping,Cai, Chun,Yi, Wen-Bin
, p. 27107 - 27111 (2015)
A newly developed C-S bond formation process via acid-catalyzed thia-Michael addition has been demonstrated. The protocol, in which Bunte salts generated from odorless and inexpensive sodium thiosulfate and organic halides are used as the thiol precursors, provides an efficient approach for the synthesis of β-sulfido carbonyl compounds.
Dithiooxamide as an Effective Sulfur Surrogate for Odorless High-Yielding Carbon-Sulfur Bond Formation in Wet PEG200 as an Eco-Friendly, Safe, and Recoverable Solvent
Firouzabadi, Habib,Iranpoor, Nasser,Gorginpour, Forough,Samadi, Arash
supporting information, p. 2914 - 2920 (2015/05/04)
In this study, we have employed dithiooxamide, a solid, odorless, and commercially available compound, as a sulfur surrogate for the preparation of dialkyl sulfides from available alkyl halides in high yields. This sulfur transfer agent was also used for a copper-catalyzed high-yielding preparation of diaryl sulfides from their available aryl halides and for the preparation of thia-Michael adducts in high yields. All the reactions were performed under odorless conditions in wet PEG200 (PEG = polyethylene glycol), which is an eco-friendly, safe, and recoverable solvent. The protocols were easily applicable to large-scale operation.
O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 758 - 767 (2013/01/15)
The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Sulfenate substitution as a complement and alternative to sulfoxidation in the diastereoselective preparation of chiral β-substituted β-amino sulfoxides
S?derman, Stefan C.,Schwan, Adrian L.
, p. 1638 - 1649 (2013/03/28)
Building from a previous communication, the reaction of sulfenate anions with chiral N-Boc-protected β-substituted β-amino iodides was evaluated as a conceptually different synthetic approach to chiral β-substituted β-amino sulfoxides. Using arenesulfenat
Pronounced catalytic effect of a micellar solution of sodium dodecyl sulfate (SDS) on the efficient C-S bond formation via an odorless thia-michael addition reaction through the in situ generation of S-alkylisothiouronium salts
Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
experimental part, p. 755 - 766 (2009/11/30)
A pronounced catalytic effect of sodium dodecyl sulfate (SDS) was observed on the in situ production of 5-alkylisothiouronium salts via the reaction of primary, allyl and benzyl halides with thiourea in SDS droplets .Hydrolysis of the generated Salkylisot
Remarkably mild and simple preparation of sulfenate anions from β-sulfinylesters: A new route to enantioenriched sulfoxides
Caupene, Caroline,Boudou, Cedric,Perrio, Stephane,Metzner, Patrick
, p. 2812 - 2815 (2007/10/03)
(Chemical Equation Presented) A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using β-sulfmylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (-)-sparteine, is also described.
Development of Odorless Thiols and Sulfides and Their Applications to Organic Synthesis
Nishide, Kiyoharu,Ohsugi, Shin-Ichi,Miyamoto, Tetsuo,Kumar, Kamal,Node, Manabu
, p. 189 - 200 (2007/10/03)
Development of new odorless thiols (dodecanethiol, 4-n- heptylphenylmethanethiol, 4-trimethylsilylphenylmethanethiol, 4-trimethylsilylbenzenethiol) and an odorless sulfide (1-methylsulfanyldodecane) and their applications to dealkylation, Michael addition, Swern oxidation, and Corey-Kim oxidation are described.
Synthetic equivalents of benzenethiol and benzyl mercaptan having faint smell: Odor reducing effect of trialkylsilyl group
Nishide, Kiyoharu,Miyamoto, Tetsuo,Kumar, Kamal,Ohsugi, Shin-Ichi,Node, Manabu
, p. 8569 - 8573 (2007/10/03)
Syntheses and odor tests of the trialkylsilylated benzyl mercaptans and benzenethiols have revealed that the trimethylsilyl substituent on the benzene ring has a remarkable effect in reducing the foul smell of the parent benzyl mercaptan and benzenethiol.
A Facile Synthesis of Functionalised Organic Sulphides
Singh, Harjit,Batra, Manohar S.
, p. 1111 - 1112 (2007/10/02)
Thioiminium salts and organic halides or Michael acceptors, in the absence of solvent and at ambient temperature, give title compounds in excellent yields.
Monomethylation of Aromatic Rings by Friedel-Crafts Reaction with Chloromethyl Sulfide
Tamura, Yasumitsu,Annoura, Hirokazu,Fuji, Masahiro,Okura, Masami,Ishibashi, Hiroyuki
, p. 540 - 549 (2007/10/02)
A novel method for the introduction of a methyl group into aromatic rings is described.Friedel-Crafts reactions of ethyl α-(chloromethylthio)acetate (3k) and α-chloromethylthio-γ-butyrolactone (3m) with an arene in the presence of stannic chloride gave ethyl α-(arylmethylthio)acetate (6) and α-arylmethylthio-γ-butyrolactone (7), respectively, which were easily converted to the corresponding methylated arene (8) by reductive desulfurization with Raney nickel or zinc dust-acetic acid.Keywords - monomethylation; ethyl α-(chloromethylthio)acetate Friedel-Crafts reaction; α-chloromethylthio-γ-butyrolactone Friedel-Crafts reaction; ethyl α-(arylmethylthio)acetate; α-arylmethylthio-γ-butyrolactone; methylated arene; reductive desulfurization; Raney nickel; zinc dust-acetic acid
