Investigation of Selective Mono-deallylation of O,O'-Diallylcatechols and 3-Methylene-1,5-benzodioxepanes
作者:Maiko Hayashida、Miyuki Ishizaki、Hiroshi Hara
DOI:10.1248/cpb.54.1299
日期:——
Selective mono-deallylation of O,O′-diallylcatechols using 10% Pd/C was investigated to give the correspond-ing allylphenols. A similar reaction of 3-methylene-1,5-benzodioxepanes afforded O-methacryl catecohols. When substrates bearing various substituents on the benzene ring were subjected to the reaction, regioselective cleavage of an ether bond occurred at the side of para position to an electron-withdrawing group on the aromatic ring. On the other hand, an electron-donating group did not cause any selectivity.
研究人员使用 10% Pd/C 对 O,O′-二烯丙基邻苯二酚进行选择性单烯丙基化反应,从而得到相应的烯丙基苯酚。3-亚甲基-1,5-苯并二氧杂环庚烷也发生了类似的反应,得到了 O-甲基丙烯酰邻苯二酚。当苯环上带有不同取代基的底物发生反应时,醚键在芳香环上对位侧与电子吸收基团发生区域选择性裂解。另一方面,电子捐赠基则没有任何选择性。