Synthesis, properties, and reactions of a stable carbanion derived from alkynyldihydrofullerene: 1-Octynyl-C-60 carbanion

被引：78

作者：

Murata, Y

Motoyama, K

Komatsu, K

Wan, TSM

机构：

[1] KYOTO UNIV,INST CHEM RES,UJI,KYOTO 611,JAPAN

[2] HONG KONG UNIV SCI & TECHNOL,DEPT CHEM,KOWLOON,HONG KONG

来源：

TETRAHEDRON | 1996年 / 52卷 / 14期

关键词：

D O I：

10.1016/0040-4020(96)00115-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stable 1-octynyl-C-60 carbanion (2(-)) was generated by the reaction of 1-octynyl-C-60-H with t-BuOK in THF, and its structure was confirmed by H-1 and C-13 NMR spectra. The redox properties were studied by cyclic voltammetry, and were shown to involve a one electron oxidation process affording a dimer of the corresponding radical, in addition to stepwise reduction processes. In accord with the results of semiempirical MO calculations (AM1), the reaction of anion 2(-) with various carbon electrophiles afforded the 1,2- or 1,4-disubstituted dihydrofullerenes. The reaction site was apparently controlled by electron density of anion 2(-) and the steric effects. (C) 1996 Elsevier Science Ltd

引用

页码：5077 / 5090

页数：14

共 21 条

[1] SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES OF C-60 FROM 1,9-(4-HYDROXYCYCLOHEXANO)-BUCKMINSTERFULLERENE [J].