High temperature bromination. Part 22: Bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene
作者:Demet Demirci-Gültekin、Duygu D. Günbaş、Yavuz Taşkesenligil、Metin Balci
DOI:10.1016/j.tet.2007.05.124
日期:2007.8
The high-temperature bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene and its carboethoxy derivative was studied. Reaction of the title compound with 1 mol of bromine in refluxing carbon tetrachloride resulted in the formation of ring-opening products. In the case of the carboethoxy derivative, bromination took place both regio- and stereospecifically at the benzylic positions, the cyclopropane
研究了1a,2,7,7a-四氢-1 H-环丙烷[ b ]萘及其碳乙氧基衍生物的高温溴化反应。标题化合物与1摩尔溴在回流的四氯化碳中反应导致开环产物的形成。在碳乙氧基衍生物的情况下,溴化是在苄基位置上在区域上和立体上都发生的,环丙烷环没有发生键断裂。讨论了产物形成及其脱氢溴化反应的机理。