ORGANOBORON COMPOUNDS .11. ISOMERIZATION OF 2,2'-TOLANDIBORONIC ACID
ORGANOBORON COMPOUNDS .11. ISOMERIZATION OF 2,2'-TOLANDIBORONIC ACID
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DOI：
10.1021/ja01521a024
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发表时间：
1959-01-01
影响因子：
15
通讯作者：
NAZY, JR
中科院分区：
文献类型：
--
作者：
LETSINGER, RL;NAZY, JR
由2,2′-二溴联苯制备的2,2′-二溴联苯胺，通过与-丁基锂、-硼酸丁酯和水的连续反应，转化为2,2′-二溴联苯酸。虽然化合物I在稀盐酸或醋酸-醋酸钠缓冲液中是稳定的，但在温和的碱性溶液或含有酒石酸氢钠的酸性溶液中，化合物I异构成新的硼酸VIII。转化的净效应是在碳碳三键上加了一个二羟基硼基。这表明，这种异构化涉及硼酸的配合物与邻近官能团的相互作用。
2, 2'-Dibromotolan, prepared from 2, 2'-dibromobibenzyl, was converted to 2, 2'-tolandiboronic acid (I) by successive re-actions with «-butyllithium,«-butyl borate and water. Although stable in thepresence of dilutehydrochloric acid or an acetic acid-sodium acetate buffer, Compound I isomerized to a new boronic acid, VIII, in mild alkaline solutions or in an acidic solution which contained sodium hydrogen tartrate. The net effect of the transformation was addition of a dihydroxy-boryl group to the carbon-carbon triple bond. It is suggested that this isomerization involves the interaction of a complex of the boronic acid with the neighboring functional group.