trans-2,2′-bi(1-phenyladamantylidene):: The most twisted biadamantylidene

被引：6

作者：

Okazaki, T ^{[1
]}

Ogawa, K ^{[1
]}

Kitagawa, T ^{[1
]}

Takeuchi, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 17期

关键词：

D O I：

10.1021/jo020247+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Grignard coupling of 2,2-dibromo-1-phenyladamantane gave trans-2,2'-bi(1-phenyladamantylidene) (1-Ph). Single-crystal X-ray analysis indicated that 1-Ph has a 23.2degrees twisted double bond, which is much more distorted than that of parent 2,2'-biadamantylidene (1-H) and that of the ethyl-substituted derivative (1-Et). A cyclic voltammogram showed a reversible electron oxidation wave at 0.87 V vs Fc/Fc(+), which is 0.19 V lower than 1-H, indicating a significant increase in the HOMO energy level due to the distortion. The reaction of 1-Ph with 0.9 equiv of bromine gave an intramolecular Friedel-Crafts alkylation product, while bromination of 1-H and 1-Me has been reported to give a bridged bromonium ion and a rearranged product, 2-(1-methyl-2-adamantylidene)4-bromotricyclo[5,3,1,0(3.9)]undec-4-ene, respectively.

引用

页码：5981 / 5986

页数：6

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