GROUND-STATE STRAIN AND OTHER FACTORS INFLUENCING OPTICAL STABILITY IN 1,1'-BINAPHTHYL SERIES
GROUND-STATE STRAIN AND OTHER FACTORS INFLUENCING OPTICAL STABILITY IN 1,1'-BINAPHTHYL SERIES
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DOI：
10.1039/jr9630002365
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发表时间：
1963-01-01
期刊：
影响因子：
--
通讯作者：
HARRIS, MM
中科院分区：
文献类型：
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作者：
COOKE, AS;HARRIS, MM
没有必要再研究1,1 '-二萘- 2,2 '-二羧酸(I)，因为Hall和Turner最近报道，虽然它在熔化时外消旋，但他们没有发现它在溶剂中不开始分解的温度下是不可能外消旋的；在175英寸的n -甲基甲酰胺中，在沸腾的四氢（2小时）中，在100英寸（10小时）或140英寸（5小时）的0- in氢氧化钠溶液中，它都能抵抗外消旋。因此，这种酸的光学稳定性可以认为是目前系列中最大的。表中提到的化合物是1,1 '-联萘基本身及其衍生物，其含有5,5 ‘，8-和S， S’-取代基。除了一种外，其他都是先以外消旋态制备的；其中四个也已获得旋光活性。在实验部分描述了合成工作，以及在这种情况下用于酸的分解或不对称转化的程序。光活性甲酯是由重氮甲烷作用于光活性酸合成的。
It was not necessary to investigate 1, l'-binaphthyl-2, 2'-dicarboxylic acid (I) again because Hall and Turner 13 have reported recently that, although it racemises on melting, they did not find it possible to racemise it in a solvent at temperatures at which it did not begin to decompose; it resisted racemisation in N-methylformamide at 175", in boiling tetrah (2 hours), and in 0-IN-sodium hydroxide solution at 100"(10 hours) or 140"(5 hours). The optical stability of this acid can therefore be regarded as by far the greatest in the present series.The compounds referred to in the Table are 1, l'-binaphthyl itself and derivatives in which it carries substituents in the 5, 5', the 8-, and the S, S'-positions. All but one had been prepared previously in the racemic state; four of them had also been obtained optically active. Synthetic work is described in the Experimental section, together with the procedure used on this occasion for the resolution or asymmetric transformation of the acids. Optically active methyl esters were made by the action of diazomethane on the optically active acids.