Studies on the Syntheses of Aliphatic Diamines. XI.:Synthesis of 1, 7-Dicyanoheptene-3

概要

論文の詳細を見る
The reaction conditions for the synthesis of 1, 7-dicyanoheptene-3 from 1, 7-dichloroheptene-3 or 1, 4, 7-trichloroheptane which was obtained through ring opening reaction of 3-(2-tetrahydrofuryl) propanol with hydrogen chloride have been investigated. When 1, 7-dichloroheptene-3 was treated with sodium cyanide by using 70-80% methyl cellosolve, ethyl cellosolve, DMSO, or methanol as a solvent, 1, 7-dicyanoheptene-3 was obtained in 90-96% yield. When this reaction was conducted in an aqueous medium containing a quarternary ammonium salt type cationic surface active agent, the yield dropped to 70%. Catalytic vapor phase reaction between 1, 7-dichloroheptene-3 and hydrogen cyanide at high temperatures in the presence of granular active carbon impregnated with metal chlorides resulted in the formation of only olefins. 1, 7-Dicyanoheptene-3, however, was obtained in 25% yield upon treatment of the 1, 7-drehloro-olefin with hydrogen cyanide in liquid ammonia. Using sodium cyanide, it was possible to convert 1, 4, 7-trichloroheptane selectively into 1, 7-dicyano-4-chloroheptane, which was then dehydrochlorinated at 250-280°C. in uacuo to give 1, 7-dicyanoheptene-3 in 73% yield.
社団法人有機合成化学協会の論文