Reaction of α-alkoxyacroleins with acetone cyanohydrin

Conclusions -Alkoxyacroleins add acetone cyanohydrin in the presence of piperidine to give 1-N-piperidino-1-cyano-2-alkoxy-2-propenes, which in the presence of piperidine or on long storage are isomerized to 1-N-piperidino-1-cyano-2-alkoxy-1-propenes.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2122–2124, September, 1973.     

Reaction of some amines with unsaturated N-acylbenzoxazolones

It is shown that the addition of aniline proceeds at the carbon-carbon double bond of N-acryloyl-, N-chloroacryloyl-, and N-methylacryloylbenzoxazolones. The basicity of the amine has a substantial effect on the course of the reaction with various amines. Transamidation of the acryloyl residue occurs with strongly basic amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1044–1048, August, 1974.     

A facile direct conversion of aldehydes to esters and amides using acetone cyanohydrin

Aromatic aldehydes with electron-withdrawing groups undergo rapid reactions with a variety of alcohols and secondary amines to afford the corresponding esters and amides, respectively, in high yields, when treated with NaCN or acetone cyanohydrin and base under ambient reaction conditions. In case of α,β-unsaturated aldehydes, simultaneous reduction of the CC bond along with esterification occurred to produce the saturated esters in high yields.     

Oxovanadium(V)-catalyzed enantioselective Meerwein-Ponndorf-Verley cyanation of aldehydes using acetone cyanohydrin

Oxovanadium(V)(salen) complex 4 was found to catalyze Meerwein-Ponndorf-Verley cyanation of aliphatic aldehydes with good to high enantioselectivity. This cyanation showed a positive nonlinear effect.     

Reaction of biacetylene with secondary amines

Conclusions The reaction of biacetylene with secondary saturated diamines proceeds predominantly with the formation of monoaddition products of both linear and cyclic structure.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1163–1164, May, 1973.     

Reaction of silylphosphites with secondary amines

The reaction of dialkylsilylphosphites with linear and cyclic secondary amines leads to the formation of acid alkoxydialkylamidophosphites and dialkyl phosphites. Aminolysis of pyrocatecholsilylphosphite was accomplished with retention of the phosphorus atom and formation of the corresponding amidophosphites.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 235–237, January, 1991.     

Reaction of citral with acetone cyanohydrin and diethylamine,and thermolysis of the resulting aminonitrile

The reactions of citral with acetone cyanohydrin and secondary amines (diethylamine, piperidine, morpholine, and N-methylaniline) to give 2-substituted amino-4, 8-dimethyl-3,7-nonadienoic acid nitriles have been examined. Possible path-ways for these reactions are discussed. The thermolysis of 2-diethylamino-4,8-dimethyl-3, 7-nonadienoic acid nitrile has been examined in solution, to give irreversibly 3-cyano-1-diethylamino-3,7-dimethyl-1,6-octadiene, this reaction proceeding faster in polar than in nonpolar solvents.The synthetic citral used contained, according to GLC, 65% of the E- and 35% of the Zisomer.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2033–2038, September, 1989.     

Utilization of acetone cyanohydrin in the reissert reaction

A modification of the Reissert reaction based on the utilization of acetone cyanohy-drin instead of potassium cyanide is proposed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 803–804, June, 1984.     

Reaction of alkoxyl organomercury compounds with secondary amines

Conclusions The reactions of the tert-butylates of n-propylmercury, isopropylmercury and phenylmercury with diethylamine are accompanied by the formation of compounds that contain the Hg-N bond. As a result, we were the first to obtain diethylaminophenylmercury. The latter reacts with chloroform at room temperature to give phenyl(trichloromethyl)mercury.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp.474–475, February, 1973.     

Reaction of triethyl trithiophosphite with aromatic aldehydes in the presence of N-phenylthiourea

Conclusions Triethyl trithiophosphite reacts with benzaldehyde and anisaldehyde in the presence of N-phenylthiourea to form S,S-diethyl-1-(N-phenylthioureo)-N-benzyldithiophosphonates.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2597–2598, November, 1987.     

Cyanation of halo derivatives by acetone cyanohydrin

A preparative method is proposed for the synthesis of substituted acetonitriles by the cyanation of halo derivatives by acetone cyanohydrin in the presence of base and phase transfer catalysts.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2647–2648, November, 1989.     

Unusual reaction of phenylpropargyl aldehyde with diethylamine and acetone cyanohydrin

Conclusions An unusual product was obtained by the reaction of phenylpropargyl aldehyde with acetone cyanohydrin and diethylamine, which has the structure of 1,6-dicyano-1,6-bis(diethylamino)-3,4-diphenyl-1,5-hexadiene.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1637–1639, July, 1979.