113436-59-2Relevant articles and documents
Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride
Kiyokawa, Kensuke,Nagata, Takaya,Hayakawa, Junpei,Minakata, Satoshi
supporting information, p. 1280 - 1285 (2015/02/19)
A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.
Synthesis and properties of azoles and their derivatives. Part LXII. Secondary deuterium kinetic isotope effects in [2+3] cycloaddition of (E)-2-phenylnitroethene to (Z)-C,N-diphenylnitrone
Baranski,Lyubimtsev,Jasinski,Kwiatkowska
, p. 1036 - 1042 (2008/09/21)
SKIE analysis of [2+3] cycloaddition of (E)-2-phenylnitroethene to (Z)-C,N-diphenyl-nitrone suggests that for both stereoisomeric reaction paths (Scheme 1 ), the 01-C5 bond of the adduct forms faster than the corresponding C3-C4 bond. Nevertheless, both s
Cycloadditions dipolaires 1,3 aux derives nitres α ethyleniques, acetyleniques potentiels. I. Reaction avec des ylures d'azomethine. Orientation et stereochimie de la cycloaddition
Benhaoua, Hadj,Piet, Jean-Claude,Danion-Bougot, Renee,Toupet, Loic,Carrie, Robert
, p. 325 - 338 (2007/10/02)
The stereochemistry of the nitroolefins 1 prepared by known methods was unambigously established.Their reactions with azomethine ylides (e.g. 8) was studied and the stereochemistry of the adducts as well.This preliminary work was necessary to substantiate a discussion of structural (pyrrolidines conformational analysis) and mechanistic problems (dipolarophile-azomethine ylide approach and HNO2 elimination from the nitro pyrrolidines).