4830-96-0Relevant articles and documents
Photoinduced, Copper-Catalyzed Carbon-Carbon Bond Formation with Alkyl Electrophiles: Cyanation of Unactivated Secondary Alkyl Chlorides at Room Temperature
Ratani, Tanvi S.,Bachman, Shoshana,Fu, Gregory C.,Peters, Jonas C.
, p. 13902 - 13907 (2015)
We have recently reported that, in the presence of light and a copper catalyst, nitrogen nucleophiles such as carbazoles and primary amides undergo C-N coupling with alkyl halides under mild conditions. In the present study, we establish that photoinduced, copper-catalyzed alkylation can also be applied to C-C bond formation, specifically, that the cyanation of unactivated secondary alkyl chlorides can be achieved at room temperature to afford nitriles, an important class of target molecules. Thus, in the presence of an inexpensive copper catalyst (CuI; no ligand coadditive) and a readily available light source (UVC compact fluorescent light bulb), a wide array of alkyl halides undergo cyanation in good yield. Our initial mechanistic studies are consistent with the hypothesis that an excited state of [Cu(CN)2]- may play a role, via single electron transfer, in this process. This investigation provides a rare example of a transition metal-catalyzed cyanation of an alkyl halide, as well as the first illustrations of photoinduced, copper-catalyzed alkylation with either a carbon nucleophile or a secondary alkyl chloride.
Interpretation of retention indices in gas chromatography for establishing structures of isomeric products of alkylarenes radical chlorination
Zenkevich
, p. 270 - 280 (2007/10/03)
By an example of previously uncharacterized products obtained by alkylarenes radical chlorination was demonstrated that combination of various interpretation methods applied to the retention indices (RI) in the gas chromatography on the standard nonpolar phases (comparison of RI of products and initial compounds, characteristics of succession of the chromatographic elution of the structural isomers with the use of estimation of molecular dynamic parameters, application of the additive schemes to RI calculation, and using of structural analogy CH3?Cl for testing the results obtained) permitted unambiguous identification of the structure even without data of mass spectrometry.
