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

Authors
Mitchell, RH Ward, TR
Citation
Rh. Mitchell et Tr. Ward, The synthesis of benz-, naphth-, and anth-annelated dihydropyrenes as aidsto measuring aromaticity by NMR, TETRAHEDRON, 57(17), 2001, pp. 3689-3695
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
17
Year of publication
2001
Pages
3689 - 3695
Database
ISI
SICI code
0040-4020(20010423)57:17<3689:TSOBNA>2.0.ZU;2-V
Abstract
Benzo[e]-, naphtho[e]- and anthro[e]-fused 2,7-di-t-butyl-trans-10b,10c-dim ethyldihydropyrenes are synthesized via an 'arynefuran' Diels-Alder reactio n and the series used to establish a relative aromaticity scale for estimat ing resonance energies (bond localization energies) using NMR chemical shif t data of the internal methyl protons of the dihydropyrenes. (C) 2001 Elsev ier Science Ltd. All rights reserved.