The chemistry of acrylonitrile IV Cyanoethylation of active hydrogen groups
The chemistry of acrylonitrile IV Cyanoethylation of active hydrogen groups
复制标题
DOI：
10.1021/ja01241a007
复制
发表时间：
1943-01-01
影响因子：
15
通讯作者：
Riener, TW
中科院分区：
文献类型：
--
作者：
Bruson, HA;Riener, TW
丙烯腈在碱性催化剂三甲基苄基氢氧化铵存在下缩合，不饱和化合物具有一个由-CO-、-CN或-CO-NH2基团活化的三碳原子脱氢体系，从而得到氰乙基化产物。以这种方式，均三甲基氧化物合成了1-(D-氰乙基)-L-异亚丙基丙酮和y-乙酰基-7-异丙烯基异亚甲腈。3.烯丙基氰化物或丁腈与丙烯腈反应生成亚乙基戊二腈和7-氰基-7-乙烯基丁腈。以丙烯腈、/3-甲基丁腈和环己叉-乙腈为典型的1，3-氢移位化合物，也得到了类似的结果。4.从上述某些腈的水解物中获得的若干多元羧酸
Acrylonitrile was condensed in the presence of aqueous trimethylbenzylammonium hydroxide as an alkaline catalyst, with unsaturated com-pounds having a three-carbon atom desmotropic system activated by a—CO—,—CN, or—CO—NH2 group, whereby cyanoethylation products were obtained.2. In this manner mesityl oxide yielded 1-(d-cyanoethyl)-l-isopropylidene-acetone and y-acetyl-7-isopropenylpimelonitrile. 3. Allyl cyanide or crotononitrile added acrylo-nitrile to yield-ethylidene glutaronitrile and 7-cyano-7-vinylpimelonÍtrile. Analogous results were obtained by treating acrylonitrile with cro-tonamide,/3-methylcrotononitrile and cyclohexylidene-acetonitrile as typical examples of com-pounds displaying a 1, 3-hydrogen shift. 4. A number of polycarboxylic acids obtained from the hydrolysis of some of the above nitriles