STUDIES IN STEREOCHEMISTRY .1. THE STEREOSPECIFIC WAGNER-MEERWEIN REARRANGEMENT OF THE ISOMERS OF 3-PHENYL-2-BUTANOL
STUDIES IN STEREOCHEMISTRY .1. THE STEREOSPECIFIC WAGNER-MEERWEIN REARRANGEMENT OF THE ISOMERS OF 3-PHENYL-2-BUTANOL
复制标题
DOI：
10.1021/ja01180a001
复制
发表时间：
1949-01-01
影响因子：
15
通讯作者：
CRAM, DJ
中科院分区：
文献类型：
--
作者：
CRAM, DJ
我们对分子重排机制的更深入的了解很大程度上依赖于对给定反应的反应物和产物中的特定碳原子基团之间存在的立体化学关系的使用。因此，沃利斯和同事3以及其他人在他们关于该主题的基础研究中明确证明，在库尔蒂斯、霍夫曼、洛森和沃尔夫重排中，迁移物种在不对称时能够在整个反应过程中保持光学构型。有充分的理由预期这种关于迁移基团的立体特异性可以同样很好地应用于频那醇和瓦格纳-米尔温重排。
A considerableamount of our more intimate knowledge of the mechanisms of molecular rear-rangements rests on the use of stereochemical re-lationships which exist between particular groups of carbon atoms in reactants and products of a given reaction. Thus Wallis and co-workers3 and others have unequivocally demonstrated in their fundamental researches on the subject that in the Curtius, Hofmann, Lossen and Wolff rearrange-ments the migrating species when asymmetric is capable of maintaining optical configuration throughout the course of the reaction. There is good reason to expect that this stereospecificity with regard to the migrating group can be equally well applied to the pinacol and Wagner-Meerwein rearrangements.