Bis 2-cyanoethyl

N-2-cyanoethylaniline has been prepared (accompanied by much of the N,N -bis-2-cyanoethyl compound) by heating aniline, acrylonitrile and acetic acid either in an autoclave, or at refluxing temperature for 10 hours in the presence of various inorganic catalysts. The substance has also been obtained, free of the N,N -bis-2-cyanoethyl compound, from aniline salts and /3-diethylaminopropionitrile. ... 

Ammonium thiocyanate, 0479 Azidoacetonitrile, 0714 2,2/-Azobis(2,4-dimethylvaleronitrile), 3668 Azoisobutyronitrile, 3011 2,2/-Azoisovaleronitrile, 3345 Bis(acrylonitrile)nickel(0), 2312 Bis(2-cyanoethyl)amine, 2397... 

Benzyl bromide, Molecular sieve, 2735 Benzyl chloride, Catalytic impurities, 2738 1,2-Bis(chloromethyl)benzene, 2946 Bis(2-cyanoethyl)amine, 2397 Bis(trimethylsilyl) peroxomonosulfate, 2602 Borane -tetrahydrofuran, 0138 Butylmagnesium chloride, 1641 Calcium acetylide, Methanol, 0585 Calcium chloride, 3923 Cerium, Water, 3961... 

Activated unsaturated compounds react with species as well [261]. Thus, acrylonitrile gives bis(2-cyanoethyl)trisulfide as a main product along with some amount of 6-amino-5-cyano-7,8-dihydro-4//-l,2,3-trithiocine, if the reaction was carried out in strong basic media (Scheme 60). 

Cyclodextrines, modified with 2-cyanoethyl and with bis(2-cyanoethyl)amino groups were used as ligands in the [PdCy + [CuCU]-catalyzed Wacker-oxidation of 1-octene. Without the modified cyclodextrins the yield of 2-octanone was less than 1 %, which could be raised to 73 % by the addition of nitrile-modified P-cyclodextrin ligands (60 °C, 2 h). 

Malonodinitrile Complex of N,N -bis(2-cyanoethyl)-l,10-diaza-4,7,13,16-tetraoxa-cyclooctadecane (5b)... 

Biphenylyl)urea, 31,10 l-(4-Biphenylyl)urea, 31,10 Bis-4-chIorobutyl ether, 37, 55 Bischloromethyl ether, 36,1 N,N -Bis-2-cyanoethyl-a-phenylene-... 

A. Preparation of bis(2-Cyanoethyl)phenylphosphine. A 250-ml. three-necked flask is equipped with a magnetic stirrer, a thermometer, a pressure-equalizing dropping funnel, and a reflux condenser with the entire system flushed with nitrogen. To the flask is added under an atmosphere of nitrogen 50.0 g. (0.454 mole) of phenylphosphine (Note 1), 50 ml. of acetonitrile, and 10 ml. of 10N potassium hydroxide (Note 2). An ice-water bath is prepared for immediate cooling of the reaction flask. To... 

B. Preparation of 4-Amino-1,2,5,6-tetrahydro-l-phenyl-phosphorin-3-carbonitrile. To a nitrogen-flushed 1-1. threenecked flask equipped with a mechanical stirrer, a pressure-equalizing addition funnel, and a reflux condenser are added 25 g. (0.22 mole) of potassium room temperature, 250 ml. of water is added, and the resulting mixture is stirred for 30 minutes while the product crystallizes. The mixture is filtered, and the solid product is washed on the filter with two 50-ml. portions of cold ethanol to give, after drying at 78° (1 mm.), 36-38 g. (84-88%) of 4-amino-1,2,5,6-tetrahydro-1 -phenylphosphorin- 3-carboni-trile, m.p. 134.5-137° (Note 9). A small amount of product can be recovered from the filtrate (Note 10). 

The intermediates, bis(2-cyanoethyl)phenylphosphine and 4-amino-l,2,5,6-tetrahydro-l-phenylphosphorin-3-carbonitrile, are easily isolated and characterized and show little or no oxidation when exposed to the air. l-Phenyl-4-phosphorinanone is a highly-crystalline material which is more sensitive to air oxidation than its two precursors. However, l-phenyl-4-phosphorinanone may be stored in a well-capped bottle for several months without appreciable oxidation. It is best stored in a dark bottle in a dry box under nitrogen. 

Hydrogen telluride, prepared from aluminum telluride and 2 molar hydrochloric acid, added to the double bond in vinyl cyanide and formed bis[2-cyanoethyl tellurium1. 

Bis[2-cyanoethyl] tellurium was also reported to be obtained from vinyl cyanide and electrolytically generated hydrogen telluride2. However, attempts to repeat this procedure failed2. 

Bis[2-cyanoethyl] tellurium was hydrolyzed by refluxing in 6 molar hydrochloric acid to bis[2-carboxyethyl] tellurium3 4. 

Bis[2-carboxyethyl] Tellurium3 In a 50-m/ flask equipped with a magnetic stirrer and a reflux condenser are placed 4g (17 mmol) of bis[2-cyanoethyl] tellurium and 10 m/ of 6M hydrochloric acid. The mixture is heated under reflux, the flask is then cooled in ice, and the crystalline precipitate is collected by filtration. Recrystallization from aqueous acetone removes tellurium from the product yield 4g (87%) m.p. 160°. 

AW—Acid washed CEF—ACV-Bis(2-cyanoethyl)formamide DEGS—Diethylene Glycol Succinate DI—Disk integrator El—Electronic integrator FI—Flame ionization Sil—Silanized TC—Thermal conductivity TCEPE—Tetracyanoethylated Pentaerythritrol ... 

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