Cyclopropyl cyanide, preparation

Cyclopropanecarboxylic acid has been prepared by the hydrolysis of cyclopropyl cyanide,3 although it is unnecessary to... 

Cyclopropyl cyanide has been prepared by therepeated distillation of 7-chlorobutyronitrile over powdered potassium hydroxide,1- 2 3 4 5 or over a mixture of sodium hydroxide and alumina. ... 

The preparation, on a small scale, of cyclopropyl cyanide from y-chlorobutyronitrile by action of sodium in liquid ammonia, or of sodium suspended in ether, has been described.7 The present directions are based upon those given by Schlatter.8... 

Bruylante , following in the steps of Henry and Dali,prepared a number of compounds by the action of the Orlgnard reagent on cyclopropyl cyanide Michlels4 worked along similar lines and like the other investigators prepared a series of alcohols. 

Methyl cyclopropyl ketone has been prepared from ethyl aceto-acetate and ethylene bromide,6 and by the action of methyl-magnesium bromide on cyclopropyl cyanide.6-7 The procedure described for its preparation from 5-chloro-2-pentanone is similar to that of Zelinsky and Dengin.8 5-Chloro-2-pentanone has been prepared by a number of methods.9 The procedure given is essentially that of Boon 10 and of Forman.11 A similar procedure has been used for the preparation of the corresponding bromo-and iodoketones.10... 

Alicyclic nitriles are prepared by the intramolecular alkylation of halo nitriles. For example, cyclopropyl cyanide is obtained in 75-90% yield by the action of sodium amide on y-chlorobutyronitrile in ether or liquid... 

The synthesis of some cyclopropylcyano phosphonate pyranosides has been described (Scheme 25). (See Vol. 24, p.l67 and Vol.22, p.l50 for a similar preparation of cyclopropyl cyanides.)... 

The low ionic character of the aluminium-silicon bond has been cleverly utilized to develop a very mild, general and effective synthesis of acyl silanes, successful for aliphatic, aromatic, heteroaromatic, a-aUcoxy, a-amino and even a-chiral and a-cyclopropyl acyl sUanes. Acyl chlorides are treated with lithium tetrakis(trimethylsilyl)aluminium or lithium methyl tris(trimethylsilyl) aluminium in the presence of copper(I) cyanide as catalyst to give the acyl silanes in excellent yields after work-up. Later improvements include the use of 2-pyridinethiolesters in place of acyl halides, allowing preparation of acyl silanes in just a few minutes in very high yields indeed (Scheme 9) °, and the use of bis(dimethylphenylsilyl) copper lithium and a dimethylphenylsilyl zinc cuprate species as nucleophiles. 

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