5,8,17,20-tetrakis(3,5-di-t-butylphenyl)-6,7,18,19-tetradehydrotetrathia[24]annulene(4.0.4.0) and its dianion: New thiophene-derived paratropic and diatropic annulenes

被引:6
作者
Kurata, H [1 ]
Baba, H [1 ]
Oda, M [1 ]
机构
[1] OSAKA UNIV, DEPT CHEM, GRAD SCH SCI, TOYONAKA, OSAKA 560, JAPAN
关键词
D O I
10.1246/cl.1997.571
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
5, 8, 17, 20-Tetrakis(3, 5-di-t-butylphenyl)-6, 7, 18, 19-tetradehydrotetrathia[24]annulene (4. 0. 4. 0) shows clear paratropicity (antiaromaticity) and highly amphoteric redox properties, whereas the dianion obtained by its alkali metal reduction strong diatropicity (aromaticity) as a novel 26 pi-electron system.
引用
收藏
页码:571 / 572
页数:2
相关论文
共 16 条
[1]   A SIMPLE ROUTE TO SULFUR-BRIDGED ANNULENES [J].
HU, ZY ;
ATWOOD, JL ;
CAVA, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8071-8075
[2]   DEHYDROANNULENES .11. SYNTHESIS AND PROPERTIES OF 3,11,14,22-TETRA-T-BUTYL-1,12-BISDEHYDRO[22]ANNULENE [J].
IYODA, M ;
NAKAGAWA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (11) :3363-3367
[3]  
KAWAGUCHI T, 1992, J APPL CRYSTALLOGR, V25, P778, DOI 10.1107/S0021889892006368
[4]   SYNTHESIS OF 5,6,17,18-BISDEHYDROTETRATHIA[24]ANNULENE[2.2.2.2] - A STRAINED PLANAR ANNULENE DEVOID OF PERIPHERAL CONJUGATION [J].
KAWASE, T ;
DARABI, HR ;
UCHIMIYA, R ;
ODA, M .
CHEMISTRY LETTERS, 1995, (07) :499-500
[5]   UBER KUMULENE .8. REDUKTION VON ACETYLEN-GLYKOLEN - DIACETYLEN-GLYKOLEN UND TRIACETYLEN-GLYKOLEN MIT ZINN-(II)-CHLORID - KUMULENE MIT NUR ZWEI AROMATISCHEN SUBSTITUENTEN [J].
KUHN, R ;
KRAUCH, H .
CHEMISCHE BERICHTE-RECUEIL, 1955, 88 (03) :309-315
[6]   UBER KUMULENE .5. [J].
KUHN, R ;
JAHN, J .
CHEMISCHE BERICHTE-RECUEIL, 1953, 86 (06) :759-763
[7]  
KUHN R, 1940, CHEM BER, V73, P1410
[8]   SYNTHESIS AND ELECTROCHEMICAL CHARACTERISTIC OF 1,2-BIS(PHENALEN-1-YLIDENE)ETHENE - AN AMPHOTERIC 4-STAGE REDOX HYDROCARBON [J].
NAKASUJI, K ;
YOSHIDA, K ;
MURATA, I .
CHEMISTRY LETTERS, 1982, (07) :969-970
[9]   THE CHEMISTRY OF PHENALENIUM SYSTEM .32. DESIGN AND SYNTHESIS OF AN AMPHOTERIC 4-STAGE REDOX HYDROCARBON BEARING PHENALENYL MOIETIES - 1,2-BIS(PHENALEN-1-YLIDENE)ETHANE [J].
NAKASUJI, K ;
YOSHIDA, K ;
MURATA, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) :1432-1433
[10]   OPTIMIZATION OF PARAMETERS FOR SEMIEMPIRICAL METHODS .1. METHOD [J].
STEWART, JJP .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1989, 10 (02) :209-220