REGIOSPECIFIC OXIDATION OF BINOR-S AND ACID-CATALYZED REARRANGEMENT OF THE PRODUCT TO THE 1ST EXAMPLE OF A PENTACYCLO[6.6.0.05,14.07,12.09,13]TETRADECANE

被引：20

作者：

PRAMOD, K

EATON, PE

GILARDI, R

FLIPPENANDERSON, JL

机构：

[1] UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637

[2] USN,RES LAB,STRUCT MATTER LAB,WASHINGTON,DC 20375

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 25期

关键词：

D O I：

10.1021/jo00312a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dimethyldioxirane has been found to oxidize the head-to-head dimer of norbornadiene (binor-S) regiospecifically, giving first the 1-ol and then the 1,9-diol of heptacyclo[8.4.0.02,7.03,5.04,8.09’13.012’14]tetradecane. Reaction of the l-ol with boron trifluoride etherate induces gross rearrangement and leads in good yield to (±)-pentacyclo-[6.6.0.05,14.07,12.09’13]tetradec-2-en-6-one, the first reported member of this new ring system. © 1990, American Chemical Society. All rights reserved.

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页码：6105 / 6107

页数：3

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