5788-17-0Relevant articles and documents
Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions
Singh, Suneel P.,O'Donnell, Jennifer S.,Schwan, Adrian L.
supporting information; experimental part, p. 1712 - 1717 (2010/07/04)
An increasing number of reactions of sulfenic acid anions are being demonstrated in the literature. As such, mild, general and reliable means for the generation of sulfenates are due. In the current paper, an addition/elimination of 2-sulfinyl acrylates using various nucleophiles is demonstrated and evaluated as a protocol for alkane- and arenesulfenate generation. Cyclohexanethiolate, methoxide and n-butyllithum each exhibit some merit for the reaction, and the thiolate is established as a mild, selective and effective reagent to release sulfenates from 2-sulfinyl acrylates. The stereospecificity of the addition/elimination of each nucleophile is recognized, and an explanation for the specificity is offered for thiolate and methoxide.
Palladium-catalyzed aerobic oxidation of terminal olefins with electron-withdrawing groups in scCO2
Jiang, Huan-Feng,Shen, Yan-Xia,Wang, Zhao-Yang
, p. 508 - 514 (2008/03/28)
Product control of palladium-catalyzed aerobic oxidation of terminal olefins with electron-withdrawing groups can be achieved through modifying reaction conditions. When the oxidant, such as CuCl2/O2, benzoquinone/O2 or O2, was present in scCO2, aerobic oxidation of terminal olefins goes smoothly. With enough MeOH and sufficient oxygen, acetalization preponderated over cyclotrimerization, while with little MeOH as co-solvent in scCO2 or no MeOH in DMF and an appropriate pressure of O2, cyclotrimerization of terminal olefins became the dominated reaction. When oxygen is absent and triethylamine was added into the reaction system, palladium-catalyzed C-N bond formation occurs to produce β-amino acid derivatives as the sole product.
β-Sulfinyl acrylate esters as a convenient source of alkane- and arenesulfenate anions
O'Donnell, Jennifer S.,Schwan, Adrian L.
, p. 6293 - 6296 (2007/10/03)
Methyl acrylate esters bearing alkane- and arenesulfinyl units on the 2-carbon liberate sulfenate anions upon nucleophilic attack. The sulfenates are readily captured through sulfur alkylation. When a sulfenate derived from R-cysteine is generated, diastereoselective benzylation is observed.
Palladium(II)-catalyzed oxidation of acrylate esters to acetals in supercritical carbon dioxide
Jia, Lanqi,Jiang, Huanfeng,Li, Jinheng
, p. 985 - 986 (2007/10/03)
The development of a new palladium(II)-catalyzed oxidation of methyl acrylate, affording methyl 3,3-dimethoxypropanoate in excellent conversion and selectivity in supercritical CO2, is presented.
STABILITE THERMIQUE ET ALCOOLYSE DE QUELQUES YLURES DE TYPE
Burgada, R.,El Khoshnieh, Y. O.,Leroux, Y.
, p. 225 - 230 (2007/10/02)
The thermal stability and alcoholysis reaction concerning ylides of the type X3P = is reported.These ylides undergo an addition reaction with methanol leading apparently to a pentacoordinated species which decomposes with or without breaking of the P-C bond.