SYNTHESIS AND PROPERTIES OF DIETHYL 5,10-DIHETERA-5,10-DIHYDROINDENO[2,1-A]INDENE-2,7-DICARBOXYLATES

被引:83
作者
KASZYNSKI, P [1 ]
DOUGHERTY, DA [1 ]
机构
[1] CALTECH,ARTHUR AMOS NOYES LAB CHEM PHYS,DIV CHEM & CHEM ENGN,PASADENA,CA 91125
关键词
D O I
10.1021/jo00071a034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.
引用
收藏
页码:5209 / 5220
页数:12
相关论文
共 76 条
[41]   STABLE FREE RADICALS .I. ISOLATION + DISTILLATION OF 1-ETHYL-4-CARBOMETHOXYPYRIDINYL [J].
KOSOWER, EM ;
POZIOMEK, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5515-&
[42]  
KOSSMEHL GA, 1986, HDB CONDUCTIVE POL 1, P364
[43]   POLYPYRROLE - TOWARDS THE DEVELOPMENT OF A CHEMICAL SYNTHESIS [J].
MARTINA, S ;
ENKELMANN, V ;
SCHLUETER, AD ;
WEGNER, G .
SYNTHETIC METALS, 1991, 41 (1-2) :403-406
[44]   The formation of thionaphthindole [J].
McClelland, EW .
JOURNAL OF THE CHEMICAL SOCIETY, 1929, :1588-1593
[45]   A NEW SYNTHESIS OF DIBENZOSELENOPHENE [J].
MCCULLOUGH, JD ;
CAMPBELL, TW ;
GOULD, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (12) :5753-5754
[46]   FUSED HETEROCYCLES FROM ORTHO-ACYLBENZENETHIOL DERIVATIVES [J].
MCKINNON, DM ;
LEE, KR .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (06) :1405-1409
[47]  
MENDENHALL GD, 1973, ORG SYNTH, V5, P829
[48]   FERROMAGNETIC MOLECULAR CHARGE-TRANSFER COMPLEXES [J].
MILLER, JS ;
EPSTEIN, AJ ;
REIFF, WM .
CHEMICAL REVIEWS, 1988, 88 (01) :201-220
[49]  
MMURTHY TS, 1961, J SCI IND RES B PH S, V20, P169
[50]  
NEWMAN MS, 1943, ORG SYNTH, V2, P428