SYNTHESIS OF DOUBLY BRIDGEHEAD SUBSTITUTED BICYCLO[1.1.1]PENTANES - RADICAL TRANSFORMATIONS OF BRIDGEHEAD HALIDES AND CARBOXYLIC-ACIDS
SYNTHESIS OF DOUBLY BRIDGEHEAD SUBSTITUTED BICYCLO[1.1.1]PENTANES - RADICAL TRANSFORMATIONS OF BRIDGEHEAD HALIDES AND CARBOXYLIC-ACIDS
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DOI：
10.1021/jo00001a058
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发表时间：
1991-01-04
影响因子：
3.6
通讯作者：
MICHL, J
中科院分区：
文献类型：
--
作者：
KASZYNSKI, P;MCMURDIE, ND;MICHL, J
描述了由相应的桥头堡碘化物3和羧酸5生成的1-双环[1.1.1]戊基桥头堡自由基11的合成转化。这些自由基相对较高的亲核性被用于与羰基化合物的反应。在制备碘化物3及其进一步转化的反应序列中，[1.1.1]螺旋桨烷(2)是最近描述的双环[1.1.1]五-1,3-二烯基二离子(8)的合成等价物。
Synthetic transformations of the 1-bicyclo[1.1.1]pentyl bridgehead radicals 11 generated from the corresponding bridgehead iodides 3 and carboxylic acids 5 are described. The relatively high nucleophilicity of these radicals was utilized in reactions with carbonyl compounds. In the reaction sequence of preparation of the iodides 3 and their further transformations, [1.1.1]propellane (2) is a synthetic equivalent of the recently described bicyclo[1.1.1]penta-1,3-dienyl dianion (8).