Unusually high ortho-selectivity in electrophilic aromatic substitution promoted by GaCl3
作者:Fumi Yonehara、Yoshiyuki Kido、Masahiko Yamaguchi
DOI:10.1039/b003215h
日期:——
4-Bis(trimethylsilyl)buta-1,3-diyne in the presence of GaCl3 reacts with aromatic hydrocarbons at −90 to −100 °C yielding 2-arylbut-1-en-3-ynes; the reactions exhibit an unusually high tendency to alkenylate the o-position of alkyl substituents; toluene, ethylbenzene and isopropylbenzene react predominantly to exclusively at the o-position while o-xylene and 1,2,3,4-tetrahydronaphthalene react at the 3 and 5-position
1,4-双(三甲基甲硅烷基)丁-1,3-二炔在 GaCl3 存在下与芳香烃在 -90 至 -100 °C 下反应,生成 2-arylbut-1-en-3-ynes;该反应表现出异常高的使烷基取代基的邻位烯基化的趋势;甲苯、乙苯和异丙苯主要仅在邻位反应,而邻二甲苯和 1,2,3,4-四氢萘分别在 3 位和 5 位反应。