60774-46-1Relevant academic research and scientific papers
Disulfide-based metal-free α-sulfanylation of ketones
Vaquer, Andrea F.,Frongia, Angelo,Secci, Francesco,Tuveri, Enrica
, p. 96695 - 96704 (2015/11/24)
An eco-friendly methodology for the direct α-sulfanylation of ketones, has been developed. The procedure, based on the use of functionalized diaryldisulfides and catalyzed by d,l-proline, represents a mild and efficient approach for the preparation of α-arylthio-ketones.
Rhodium-catalyzed methylthio transfer reaction between ketone α-positions: Reversible single-bond metathesis of C-S and C-H bonds
Arisawa, Mieko,Suwa, Katsunori,Yamaguchi, Masahiko
supporting information; experimental part, p. 625 - 627 (2009/08/14)
(Chemical Equation Presented) In the presence of a catalytic amount of RhH(PPh3)4 and 1,2-bis(diphenylposphino)ethane (dppe), α-phenylthio ketones were methylthiolated with ρ-cyano-α- methylthioacetophenone giving α-phenylthio-α-meth
Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity
Billings, Susan B.,Woerpel
, p. 5171 - 5178 (2007/10/03)
The reactions of cyclohexanone acetals substituted with thiophenyl groups (and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.
Stereochemical behaviors of cyclohexyl α-sulfonyl carbanions
Tanikaga, Rikuhei,Nishikawa, Takeshi,Tomita, Naoki
, p. 1057 - 1062 (2007/10/03)
Diastereoisomeric 4-(t-butyl)-1-(phenylsulfonyl)cyclohexanes 3 and 4- (t-butyl)-2-phenylsulfonyl-1-cyclohexanols 10 were subjected to H-D exchange, methylation, and allylation. The anions generated from 3 and 10 rapidly isomerized to those having a sulfonyl group in an equatorial position to form both equatorial and axial carbanions, in which a slight difference was found toward the subsequent electrophilic attack. The reaction of the dianion of 10 was little affected by an adjacent oxyanion and its countercation. The steric requirement of a bulky aggregate containing a sulfonyl group and a THF- solvated metal counterion may play an important role in the stereochemical behavior of α-sulfonyl carbanions.
Diastereoselective Sulfenylation Reactions Employing N-(Phenylthio)lactams under Nonbasic Conditions
Wilson, Lawrence J.,Liotta, Dennis C.
, p. 1948 - 1950 (2007/10/02)
Silyl enol ethers and silyl ketene acetals react with sulfenamides in the presence of trimethylsilyl triflate to give the corresponding trans-sulfenylated ketones and lactones.
Alkyl Migration in Competition with Phenylthio Migration in the Acid-catalysed Rearrangement of Alcohols
Hannaby, Malcolm,Warren, Stuart
, p. 3007 - 3014 (2007/10/02)
Sulfonate derivatives of conformationally rigid syn-2-phenylthiocyclohexanols, which are prevented from phenylthio migration by stereochemistry, rearrange slowly by alkyl migration or ring contraction.In contrast to other electronegative groups, phenylthio slows the reaction down but allows migration of other groups.
Stereoselective Reductions of 2-Keto Sulfoxides with Hydrides
Carreno, M. Carmen,Ruano, Jose L. Garcia,Martin, Ana M.,Pedregal, Concepcion,Rodriguez, Jesus H.,et al.
, p. 2120 - 2128 (2007/10/02)
The results of reductions of some acyclic 2-keto sulfoxides (ArC(O)CH2S(O)R; Ar=Ph, 2-Py, 4-Py, and R=Me, p-Tol) and flexible and rigid 2-sulfinylcyclohexanone diastereomers with various metal hydrides are reported.The configurational assignment and confo
Thiosulfonic S-Esters; 6. Fluoride-Mediated α-Phenylsulfenylation of Cyclic Ketones and Esters via their Trimethylsilyl Enol Ethers
Caputo, Romualdo,Ferreri, Carla,Palumbo, Giovanni
, p. 464 - 466 (2007/10/02)
Ketones and carboxylic acid esters are conveniently converted to their α-sulfenylated derivatives.This new procedure is likely to represent the first reliable one for regiospecific monosulfenylation of carbonyl compounds.It is based on the reaction of the
Pd(O) PROMOTED ALKYLATION OF ENOL PHOSPHATES WITH ORGANOALUMINIUM COMPOUNDS AND ITS SYNTHETIC APPLICATIONS
Sato, Mitsuyoshi,Takai, Kazuhiko,Oshima, Koichiro,Nozaki, Hitosi
, p. 1609 - 1612 (2007/10/02)
Keto carbonyl 1,2- and 1,3-transpositions with and without alkylation of the substrate are described together with ketone synthesis from thiocarboxylic S-ester.
