Versuche zur Erzeugung von 1,5- und 2,3-Didehydroquadricyclanen
Versuche zur Erzeugung von 1,5- und 2,3-Didehydroquadricyclanen
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1,5- 和 2,3-二脱氢四环烷的验证
DOI：
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发表时间：
1990
期刊：
影响因子：
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通讯作者：
Günter Szeimies
中科院分区：
文献类型：
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作者：
Ulrich Heywang;Günter Szeimies
1.5-和2.3-二脱氢四环化合物的生成实验
Experiments towards the Generation of 1.5- and 2.3-Didehydroquadricyclanes
Metalation of the (hydroxymethyl)quadricyclanes 7a-c with n-butyllithium in ether is determined mostly by the chelating effect of the CH2O–Li group and only to a lesser extent by the magnitude of the 13C-1H coupling constant of the position to be lithiated in the corresponding quadricyclane derivative. Similar results were obtained for 3-quadricyclanol (20a). Treatment of the bromide 26a, prepared by lithiation of 7b, with strong bases apparently generates the 1,2-didehydroquadricyclane 34 and not the 1,5-didehydroquadricyclane 35. Attempts to convert the dihalide 9 into the 2,3-didehydroquadricyclane 4 were unsuccessful.