51392-60-0Relevant articles and documents
An efficient and straightforward route to terminal vinyl sulfones via palladium-catalyzed Suzuki reactions of α-bromo ethenylsulfones
Fang, Yewen,Yuan, Meijuan,Zhang, Juncong,Zhang, Li,Jin, Xiaoping,Li, Ruifeng,Li, Jinjian
supporting information, p. 1460 - 1463 (2016/03/12)
A general and simple protocol for the synthesis of α-substituted alkenylsulfones has been developed firstly via palladium-catalyzed Suzuki reactions between α-bromo ethenylsulfones and organoborons. Using a catalyst composed of Pd(OAc)2 and SPhos, a variety of aryl, heteroaryl, and alkylboron reagents could efficiently couple with α-bromo ethenylsulfones under mild conditions. Moreover, it has been demonstrated for the first time that vinyl sulfones underwent smooth reduction by diimide generated from 2-nitrobenzenesulfonylhydrazide.
Reaction of singlet oxygen with some benzylic sulfides
Bonesi, Sergio M.,Fagnoni, Maurizio,Monti, Sandra,Albini, Angelo
, p. 10716 - 10723 (2007/10/03)
Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.
Photosensitized oxygenation of some benzyl sulfides. The role of persulfoxide
Bonesi, Sergio M.,Freccero, Mauro,Albini, Angelo
, p. 703 - 707 (2007/10/03)
Benzyl ethyl sulfide (6a) is photo-oxidized to benzaldehyde in benzene, whereas diethyl sulfide is known to give inefficiently the sulfoxide under these conditions. Oxidative C-S cleavage is the main process also with benzhydryl ethyl sulfide (6c), but not with α-methylbenzyl ethyl sulfide (6b), which mainly gives the sulfoxide. The carbonyl derivatives reasonably arise from S-hydroperoxy ylides (3). Consistently with this finding, calculations at the PM3 level suggest that the first intermediate, the persulfoxide (1), undergoes intramolecular hydrogen transfer when an activated α-hydrogen is available and gives 3. This is the case for the above benzyl sulfides (ΔH* for the process decreases with decreasing C-H BDE). However, only some of the persulfoxide conformations are correctly oriented for this rearrangement, and this may slow this process and make other reactions compete, as happens with 6b. Copyright
