The synthesis of benz-, naphth-, and anth-annelated dihydropyrenes as aids to measuring aromaticity by NMR

被引：30

作者：

Mitchell, RH ^{[1
]}

Ward, TR ^{[1
]}

机构：

[1] Univ Victoria, Dept Chem, Victoria, BC V8W 3V6, Canada

来源：

TETRAHEDRON | 2001年 / 57卷 / 17期

关键词：

furan; annulene; Diels-Alder; aryne; resonance energy;

D O I：

10.1016/S0040-4020(01)00233-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzo[e]-, naphtho[e]- and anthro[e]-fused 2,7-di-t-butyl-trans-10b,10c-dimethyldihydropyrenes are synthesized via an 'arynefuran' Diels-Alder reaction and the series used to establish a relative aromaticity scale for estimating resonance energies (bond localization energies) using NMR chemical shift data of the internal methyl protons of the dihydropyrenes. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3689 / 3695

页数：7

共 29 条

[1]

CREMER D, 1972, LIEBIGS ANN CHEM, V763, P87

[2] DIENOPHILIC REACTIONS OF AROMATIC DOUBLE BONDS IN THE SYNTHESIS OF BETA-SUBSTITUTED NAPHTHALENES [J].

DANISH, AA ;

SILVERMAN, M ;

TAJIMA, YA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (23) :6144-6150

[3] GROUND STATES OF CONJUGATED MOLECULES .11. IMPROVED TREATMENT OF HYDROCARBONS [J].

DEWAR, MJS ;

DELLANO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (04) :789-&

[4] ORGANIC CHEMISTRY OF A NEW WEAK FIELD TRIDENTATE CHELATING AGENT . 3,5-DI(2-PYRIDYL)-1,2,4-TRIAZOLE [J].

GELDARD, JF ;

LIONS, F .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (01) :318-&

[5]

GORELIK MV, 1990, RUSS CHEM REV, P59

[6] APPLICATION OF BIOT-SAVART LAW TO RING CURRENT ANALYSIS OF PROTON CHEMICAL-SHIFTS .1. COMPREHENSIVE INVESTIGATION OF ANNULENES [J].

HADDON, RC .

TETRAHEDRON, 1972, 28 (14) :3613-&

[7] AROMATICITY OF ANNULENOANNULENES [J].

HESS, BA ;

SCHAAD, LJ ;

AGRANAT, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (17) :5268-5271

[8] Aromaticity as a quantitative concept. 7. Aromaticity reaffirmed as a multidimensional characteristic [J].

Katritzky, AR ;

Karelson, M ;

Sild, S ;

Krygowski, TM ;

Jug, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5228-5231

[9] Aromaticity:: A theoretical concept of immense practical importance [J].

Krygowski, TM ;

Cyrañski, MK ;

Czarnocki, Z ;

Häfelinger, G ;

Katritzky, AR .

TETRAHEDRON, 2000, 56 (13) :1783-1796

[10] DIHYDROPYRENES - FURTHER INSIGHT INTO EFFECTS OF ANNULENOANNELATION, BENZANNELATION, CONJUGATION AND ISOANNELATION [J].

LAI, YH ;

CHEN, P ;

PECK, TG .

PURE AND APPLIED CHEMISTRY, 1993, 65 (01) :81-87

← 1 2 3 →