113675-06-2Relevant academic research and scientific papers
METHOXYCHLORINATION AND DIMETHOXYLATION OF ALKENES. THE REACTIONS OF SUBSTITUTED STYRENES WITH PHENYLSELENENYL CHLORIDE IN METHANOL
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Bartoli, Donatella
, p. 2261 - 2272 (2007/10/02)
The addition of PhSeCl to α- and β-substituted styrenes in methanol is regio- and stereospecific and affords the products of methoxyselenenylation.These compounds further react with PhSeCl to give the deselenenylation products.In the case of α-substituted styrenes, 1-methoxy, 2-chloroalkanes are produced, whereas with β-substituted styrenes the major reaction products are the 1,2-dimethoxyalkanes and the 2,2-dimethoxyalkanes in which phenyl migration has occured.It is shown that these reactions proceed through the intermediate formation of the alkyl phenylselenium dichlorides, PhCR(OMe)CHR1SeCl2Ph, which evolve with different mechanisms depending on the structure of the starting alkenes.
CONVERSION OF ALKYL PHENYL SELENIDES AND SELENOXIDES INTO DIALKYL ETHERS. NUCLEOFUGACITY ENHANCEMENT OF THE PLENYLSELENINYL GROUP BY meta-CHLOROPERBENZOIC ACID IN ALCOHOLS
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Bartoli, Donatella
, p. 423 - 428 (2007/10/02)
The recently reported conversion of alkyl phenyl selenides into dialkyl ethers, promoted by MCPBA in alcohols, has been reinvestigated.It is concluded that the reactive intermediate does not derive from the selenones, as reported, but from the selenoxides.It is suggested that MCPBA adds to the selenoxide function to give an intermediate which easily gives rise to solvolysis; thus, the addition of MCPBA greatly enhances the nucleofugacity of the phenylseleninyl group.The synthesis and the reactivity of several 1-phenyl, 2-phenylseleninyl- and 1-phenyl-, 2-phenylselenonyl-ethanes are also described.
