化学学报 ›› 1958, Vol. 24 ›› Issue (2): 147-150. 上一篇    下一篇

论文

双(2,4,6-三甲苯)二酮及其衍生物Ⅴ.——2,5-二溴-1,6-双(2,4,6-三甲苯)己二酮-[1,6]的去溴化氢反应

高济宇, 曾成   

  1. 南京大学化学系
  • 投稿日期:1957-09-04 发布日期:2013-06-03

DIMESITYL DIKETONES AND THEIR DERIVATIVES Ⅴ. DEHYDROBROMINATION OF 2, 5-DIBROMO-1, 6-DIMESITYL HEXANDIONE-[1, 6]

KAO TSI-YU, TSENG CHEN   

  1. Department of Chemistry, Nanking University
  • Received:1957-09-04 Published:2013-06-03

实验证明2,5-二溴-1,6-双(2,4,6-三甲苯)己二酮-[1,6]在硷性试剂(吡啶)存在时,不生成五碳环衍生物,也不生成季铵盐,但脱去溴化氢而生成1,6-双(2,4,6-三甲苯)己二烯-2,4-二酮-[1,6]。其结构由催化加氢生成1,6-双(2,4.6-三甲苯)己二酮-[1.6],加溴生成1.6-双(2,4.6-三甲苯)-2,3,4,5-四溴己二酮-[1,6],和由己二烯-2,4-二酰氯和1,3,5-三甲苯的合成而得到证明。

Differing from its diphenyl analog,2,5-dibromo-1,6-dimesityl hexandione-[1,6],formed neither cyclopentane derivatives nor pyridinium salts,dehydrobromination product,1,6-dimesityl hexadiene-2,4-dione-[1,6] but the when it was treated with pyridine at about 140°.1,6-Dimesityl hexadiene-2,4-dione-[1,6] so obtained was golden yellow needles,melting at 218-219°.It contained no bromine and decolorized both alkaline permanganate and bromine solutions.Its molecular weight (338)was found close to the theoretical value (346) by Rast camphor method.It gave 1,6-dimesityl hexanedione-[1,6] by catalytic hydrogenation and 1,6-dimesityl 2,3,4,5-tetrabromohexanedione-[1,6] by addition of bromine.Its structure was finally proved by synthesis from muconyl chloride and mesitylene by Friedel-Crafts reaction.