ACID-CATALYZED DEHYDRATION OF SUBSTITUTED DIENEDIOLS
ACID-CATALYZED DEHYDRATION OF SUBSTITUTED DIENEDIOLS
复制标题
取代二烯二醇的酸催化脱水
DOI：
10.1021/jo00131a021
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发表时间：
1995
影响因子：
3.6
通讯作者：
D. E. Lehman
中科院分区：
文献类型：
--
作者：
C. Wigal;J. D. Mckinley;J. Coyle;D. J. Porter;D. E. Lehman
醌与过量的烷基锂反应，得到二烯二醇加合物。1· 2最近，这些加合物的酸催化脱水被报道为制备2，4-二烷基苯酚的合成途径。3.虽然这种脱水反应具有区域特异性合成多取代酚的潜力，但多取代酚被广泛用作抗氧化剂和稳定剂，4迄今为止研究的唯一二烯二醇是由苯醌衍生的。在本文中，我们证明了由取代的醌衍生的二烯二醇脱水得到的产物作为电子效应和取代基与碳阳离子中间体的接近度的函数而变化。h3c oh ch3 ch3 CH
Quinones react with excess alkyllithium to give diene-diols as adducts. 1· 2 Recently, the acid-catalyzed dehydration of these adducts was reported as a synthetic pathway for the preparation of 2, 4-dialkylphenols. 3 While this dehydration reaction has potential for regiospecific syn-thesis of polysubstituted phenols, which are widely used as antioxidants and stabilizers, 4 the only dienediols studied to date havebeen derivedfrom benzoquinone. In this paper, we demonstrate that the products obtained from the dehydration of dienediols derived from substi-tuted quiñones vary as a function of the electronic effects and proximity of the substituents to the carbocation intermediate. h3c oh ch3 ch3 CH