Thermal generation and (inter)conversion of (multi) cyclopenta-fused polycyclic aromatic hydrocarbons

被引:61
作者
Jenneskens, LW
Sarobe, M
Zwikker, JW
机构
[1] Debye Institute, Dept. of Physical Organic Chemistry, Utrecht University, 3584 CH Utrecht
关键词
D O I
10.1351/pac199668020219
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
FVT of 1,1-dichloro- and/or 1-chloroethenyl substituted PAH's gives access to the CP-PAH's pyracylene (1), cyclopenta[cd]pyrene (12) and benz[ghi]fluoranthene (13), cyclopent[hi] aceanthrylene (18) and cyclopent [hi]acephenanthrylene (19), and the novel cyclopenta[cd]fluoranthene (22) and isomeric cyclopent[fg]- (25a), cyclopent[jk]-(25b) and cyclopent[mn]acepyrylene (25c), respectively. The propensity of CP-PAH's to interconvert under high temperature FVT conditions is illustrated. Possible mechanisms, such as ring-contraction/ring-expansion via 1,2-H and 1,2-C are discussed.
引用
收藏
页码:219 / 224
页数:6
相关论文
共 25 条
[1]  
BELZ T, 1994, ANGEW CHEM INT EDIT, V33, P1866, DOI 10.1002/anie.199418661
[2]  
BROWN RFC, 1993, SYNLETT, P9
[3]   THE ETHYNE-ETHYLIDENE REARRANGEMENT - FORMATION OF 3-ETHYNYLACENAPHTHYLENE AND 1-ETHYNYLACENAPHTHYLENE ON FLASH VACUUM PYROLYSIS OF 1,7-DIETHYNYLNAPHTHALENE [J].
BROWN, RFC ;
EASTWOOD, FW ;
WONG, NR .
TETRAHEDRON LETTERS, 1993, 34 (07) :1223-1226
[4]  
BROWN RFC, 1980, ORGANIC CHEM MONOGRA, V41
[5]   ON THE MECHANISM OF FULLERENE FORMATION - TRAPPING OF SOME POSSIBLE INTERMEDIATES [J].
CHANG, TM ;
NAIM, A ;
AHMED, SN ;
GOODLOE, G ;
SHEVLIN, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) :7603-7604
[6]   NOTE ON FOURFOLD HX-ELIMINATION FROM PERI-TETRAKIS(CHLOROMETHYL)-AROMATIC COMPOUNDS BY FLASH VACUUM PYROLYSIS [J].
DEHMLOW, EV ;
FRUND, M .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1992, 47 (11) :1647-1648
[7]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[8]   MOLECULAR AND ELECTRONIC-STRUCTURE OF PYRACYLENE [J].
FREIERMUTH, B ;
GERBER, S ;
RIESEN, A ;
WIRZ, J ;
ZEHNDER, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :738-744
[9]   NEW LIGHT ON THE CASE OF IMPERFECT COMBUSTION [J].
KROTO, HW .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1991, 87 (18) :2871-2875
[10]   C60 - BUCKMINSTERFULLERENE [J].
KROTO, HW ;
ALLAF, AW ;
BALM, SP .
CHEMICAL REVIEWS, 1991, 91 (06) :1213-1235