Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon

被引:34
作者
Adamson, GA
Rees, CW
机构
[1] Department of Chemistry, Imperial College of Science, Technology and Medicine
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 13期
关键词
D O I
10.1039/p19960001535
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe efforts towards the synthesis of some allotropes of carbon, the cyclo[n]carbons where 18, 24 and 30. The key intermediate 11 is hexa-1,3,5-triyne with the central triple bond masked as a 1-amino-1,2,3-triazole derivative. Cyclo-oligomerisation of this by oxidative coupling gives macrocyclic precursors of C-18, C-24 and C-30. C-30 is a proposed intermediate in the formation of C-60 and we also describe some attempts at the synthesis of C-60 via the chemical generation of benzotriyne, cyclo[6]carbon.
引用
收藏
页码:1535 / 1543
页数:9
相关论文
共 33 条
[1]  
[Anonymous], COMMUNICATION
[2]  
BAUM RM, 1992, CHEM ENG NEWS 0601, P25
[3]   REACTIONS BETWEEN AZOLIUM SALTS AND NUCLEOPHILIC REAGENTS .I. BROMO-1,2,3-TRIAZOLIUM SALTS AS BROMINATING REAGENTS [J].
BEGTRUP, M ;
KRISTENS.PA .
ACTA CHEMICA SCANDINAVICA, 1969, 23 (08) :2733-&
[4]  
BROWN RFC, 1967, AUST J CHEM, V20, P139
[5]   REACTIVE INTERMEDIATES .I. SYNTHESIS AND OXIDATION OF 1- AND 2-AMINOBENZOTRIAZOLE [J].
CAMPBELL, CD ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05) :742-&
[6]   ORTHO-ACYLHYDROXYLAMINES .1. SYNTHESIS OF ORTHO-BENZOYLHYDROXYLAMINE [J].
CARPINO, LA ;
GIZA, CA ;
CARPINO, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (04) :955-957
[7]   SYNTHETIC ROUTES TO THE CYCLO[N]CARBONS [J].
DIEDERICH, F ;
RUBIN, Y ;
CHAPMAN, OL ;
GOROFF, NS .
HELVETICA CHIMICA ACTA, 1994, 77 (05) :1441-1457
[8]   SYNTHETIC APPROACHES TOWARD MOLECULAR AND POLYMERIC CARBON ALLOTROPES [J].
DIEDERICH, F ;
RUBIN, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (09) :1101-1123
[9]   ALL-CARBON MOLECULES - EVIDENCE FOR THE GENERATION OF CYCLO[18]CARBON FROM A STABLE ORGANIC PRECURSOR [J].
DIEDERICH, F ;
RUBIN, Y ;
KNOBLER, CB ;
WHETTEN, RL ;
SCHRIVER, KE ;
HOUK, KN ;
LI, Y .
SCIENCE, 1989, 245 (4922) :1088-1090
[10]  
FOSSATELLI M, 1992, SYNTHESIS-STUTTGART, P756