32787-76-1Relevant academic research and scientific papers
Catalytic hydrophosphorylation of alkyl- and acylhydrazones
Matveeva,Podrugina,Kolesnikova,Prisyazhnoi,Karateev,Zefirov
experimental part, p. 418 - 424 (2011/02/17)
N-Boc- and N-acylhydrazino phosphonates were obtained for the first time by hydrophos- phorylation of the appropriate hydrazones of aliphatic and aromatic aldehydes and heterocyclic and aliphatic ketones in the presence of [tetra(tert-butyl)phthalocyanine
A general one-pot, three-component mono N-alkylation of amines and amine derivatives in lithium perchlorate/diethyl ether solution
Heydari, Akbar,Tavakol, Hossein,Aslanzadeh, Saied,Azarnia, Jamshid,Ahmadi, Nafiseh
, p. 627 - 633 (2007/10/03)
An efficient, general procedure for reductive monoalkylation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O-trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithium perc
Unsymmetrical dimethylhydrazine in phosphorylation reactions
Ryapisova
, p. 1533 - 1535 (2007/10/03)
The reaction of dialkyl hydrogen phosphites with nitrobenzaldehyde dimethylhydrazone leads to formation of compounds having a salt-like structure, while the reaction with hydrazones gives phosphonates. α-Dimethylhydrazinophosphonates were obtained by the
Elimination Reactions of Hydrazonium Salts: Experimental and Theoretical Evidence for a Large Stereoelectronic Effect of Nitrogen
Nguyen, Minh Tho,Clarke, Leo F.,Hegarty, Anthony F.
, p. 6177 - 6183 (2007/10/02)
Elimination of trimethylamine from hydrazonium salts (8, R = Me) is promoted by base (methoxide ion in methanol).The mechanism is characterized as E2 as shown by substituent effects (ρ = +2.57), Broensted coefficients, a primary kinetic isotope effect (kH/kD = 2.10), and solvent effects.Variation in the leaving group (8, R = arylmethyl) shows that N-N bond cleavage is less well advanced in the transition state than C-H bond breaking.The elimination to give the nitrile is syn-periplanar and, using the phthalazinium salt 4 as a model for the anti elimination, an anti/syn ratio of ca. 102 is found.The reactions have been modelled using ab initio methods with the transition structures located at the HF/3-21G level and relative energies computed using the MP2/6-31G* method.Using both H2O and NH3 as model bases to induce elimination on +, the calculated energy for anti elimination is lower (in the range 11-13 kcal mol-1) than that for syn elimination.The implications of the results for the ease of formation of nitriles from aldehydes via the hydrazonium salt route are discussed.
