Synthesis of the elusive dibenzannelated dihydropyrene dibenzo[e,l]dimethyldihydropyrene, a molecular photo-switch.

被引:21
作者
Mitchell, RH
Chen, YS
机构
[1] Department of Chemistry, University of Victoria, Victoria, BC V8W 3V6
关键词
D O I
10.1016/0040-4039(96)01074-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of the unknown o-m-o-m-cyclophane derivative 13 is achieved by deoxygenation of the adduct 12, derived from a bis-Diels-Alder addition of furan to the intermediate bis-aryne generated by bis-dehydrobromination of dibromide 11. The colorless photochromic cyclophanediene 13 switches to the green dibenzannulene 14 on uv irradiation, and 14 thermally or photochemically reverts to 13, with E(act) = 20 kcal/mole. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5239 / 5242
页数:4
相关论文
共 17 条
[1]   PHOTOISOMERIZATION OF TRANS-15,16-DIMETHYLDIHYDROPYRENE [J].
BLATTMAN.HR ;
MEUCHE, D ;
HEILBRON.E ;
MOLYNEUX, RJ ;
BOEKELHE.V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (01) :130-&
[2]   PHOTOTROPY OF TRANS 15,16-DIMETHYLDIHYDROPYRENE AND ITS DERIVATIVES [J].
BLATTMANN, HR ;
SCHMIDT, W .
TETRAHEDRON, 1970, 26 (24) :5885-+
[3]  
MIOTCHELL RH, 1996, IN PRESS J ORG CHEM
[4]   BENZANNELATED ANNULENES .8. TOWARD THE UNDERSTANDING OF BENZANNELATED ANNULENES - SYNTHESIS AND PROPERTIES OF [A,H]-RING AND [A,I]-RING DIBENZANNELATED DIHYDROPYRENES [J].
MITCHELL, RH ;
WILLIAMS, RV ;
DINGLE, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2560-2571
[5]   AN EXPERIMENTAL ESTIMATION OF AROMATICITY RELATIVE TO THAT OF BENZENE - THE SYNTHESIS AND NMR PROPERTIES OF A SERIES OF HIGHLY ANNELATED DIMETHYLDIHYDROPYRENES - BRIDGED BENZANNULENES [J].
MITCHELL, RH ;
IYER, VS ;
KHALIFA, N ;
MAHADEVAN, R ;
VENUGOPALAN, S ;
WEERAWARNA, SA ;
ZHOU, PZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (05) :1514-1532
[6]   BENZANNELATED ANNULENES .2. SYNTHESIS OF TRANS-12B, 12C-DIMETHYL-12B, 12C-DIHYDROBENZO(E)PYRENE - INDICATION OF EXCEPTIONAL AROMATICITY OF 15,16-DIMETHYLDIHYDROPYRENE2 SYSTEM [J].
MITCHELL, RH ;
YAN, JSH .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (18) :3347-3348
[8]   N-BROMOSUCCINIMIDE-DIMETHYLFORMAMIDE - MILD, SELECTIVE NUCLEAR MONO-BROMINATION REAGENT FOR REACTIVE AROMATIC-COMPOUNDS [J].
MITCHELL, RH ;
LAI, YH ;
WILLIAMS, RV .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4733-4735
[9]   CLEAR DEMONSTRATION OF IMPORTANCE OF SYMMETRICAL KEKULE STRUCTURES TO DIATROPICITY (AROMATICITY) - SYNTHESIS OF A STABLE, HIGHLY DIATROPIC, DIBENZANNULENE [J].
MITCHELL, RH ;
CARRUTHERS, RJ ;
MAZUCH, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (03) :1007-1008
[10]   BENZANNELATED ANNULENES .6. TOWARD THE UNDERSTANDING OF BENZANNELATED ANNULENES - SYNTHESIS AND PROPERTIES OF [A]-RING MONOBENZANNELATED DIHYDROPYRENES [J].
MITCHELL, RH ;
CARRUTHERS, RJ ;
MAZUCH, L ;
DINGLE, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2544-2551