Cyclopropanes. XIII. The Absolute Configuration of 1-Methyl-2,2-diphenylcyclopropane
Cyclopropanes. XIII. The Absolute Configuration of 1-Methyl-2,2-diphenylcyclopropane
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环丙烷。
DOI：
10.1021/ja00883a040
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发表时间：
1962
影响因子：
15
通讯作者：
C. G. Pitt
中科院分区：
文献类型：
--
作者：
H. Walborsky;C. G. Pitt
通过与(+)- r -环氧丙烷和(-)- s -2-甲基- 3,3 -二苯基丙酸的直接化学关系，确定了l-ii -2- 2,2 -二苯基环丙烷的绝对构型。后者的绝对构型由相应的甲基酮、醛和多聚硫代氨基硫脲衍生物的旋光色散曲线确定。上述发现与先前基于部分不对称合成结果的2,2 -二苯基环丙基羧酸的绝对构型的暂定分配进行了比较。如果假设在向丙烯酸甲酯和甲基丙烯酸甲酯加成重氮二苯基甲烷时发生了“重氮交换”反应，则表明化学相关和不对称合成的结果是相容的。
The absolute configuration ofl-iiictliyi-2, 2-diphenylcyclopropane has been determined by a direct chemical correlation with (+)-R-propylene oxide and with (—)-S-2-methyl-3, 3-diphenylpropionic acid. The absolute configuration of the latter was established from the optical rotatory dispersion curves of the corresponding methyl ketone, aldehyde and mor-pliolinothiocarbamide derivatives. The above findings are compared with a previous tentative assignment of absolute configuration to 2, 2-diphenyicyclopropanecarboxylic acid, which hadbeen based on the results of partial asymmetric syntheses. The results of the chemical correlation and the asymmetric syntheses are shown to be compatible if one assumes that a “diazo-exchange” reaction has occurred in the addition of diazodiphenylmethane to the menthyl acrylate and methacrylate.