MOLECULAR ASYMMETRY OF OLEFINS .1. RESOLUTION OF TRANS-CYCLOOCTENE

MOLECULAR ASYMMETRY OF OLEFINS .1. RESOLUTION OF TRANS-CYCLOOCTENE
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DOI:
10.1021/ja00903a049
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发表时间:
1963-01-01
影响因子:
15
通讯作者:
GANELLIN, CR
GANELLIN, CR
中科院分区:
化学1区
文献类型:
--
作者:
COPE, AC;WINKLER, HJS;GANELLIN, CR

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通过含有光学活性甲基苄胺的铂配合物,完成了ZraŦs-cyclooctene的拆分。< raŧí-dichloro-(ZroŦí-cyclooctene)-[(+或-)-甲基苄胺]-铂(II)的分离分馏结晶进行恒定旋转。配合物用氰化钾溶液破坏,得到光学活性的(-)和(+)-ZraŦs-cyclooctene。这种新型的不对称表明,zraros -烯烃键不能相对于分子的其余部分旋转。
Resolution of ZraŦs-cyclooctene has been accomplished through platinum complexes containingoptically active-methylbenzylamine. Separate fractionalcrystallizations of< raŧí-dichloro-(ZroŦí-cyclooctene)-[(+ or—)--methylbenzylamine]-platinum (II) were carried out to constant rotation. The complexes were destroyed with aqueous potassium cyanide, yielding optically active (—)-and (+)-ZraŦs-cyclooctene. This noveltype of asymmetry demonstrates the inability of the Zraros-olefinic linkage to rotate with respect to the rest ofthe molecule.