CARBONIUM ION-SILANE HYDRIDE TRANSFER REACTIONS .2. 2-PHENYL-2-NORBORNYL CATION

被引：38

作者：

CAREY, FA

TREMPER, HS

机构：

[1] Department of Chemistry, University of Virginia, Charlottesville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 01期

关键词：

D O I：

10.1021/jo00838a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-phenyl-2-norbornyl cation (I) was generated from exo-2-phenyl-endo-2-norbornanol (4), entio-2-phenylezo-2-norbornanol (5), and 2-phenylnorbornene (8) in methylene chloride-trifluoroacetic acid. Under these conditions 1 abstracted hydride from triethylsilane, triphenylsilane, and phenylsilane to give exclusively the product from exo-hydride transfer, 2-endo-phenylnorbornane (6). The results indicate that exo attack on classical norbornyl cations is preferred and is not a consequence of bridging. The preparations of 5 and 6 are described. © 1969, American Chemical Society. All rights reserved.

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页码：4 / &

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