ATROPISOMERISM OF COFACIAL PYRIDINE RINGS - SYNTHESIS, PROTON NMR-SPECTRA AND CONFORMATIONS OF 1,8-DI(3'-PYRIDYL)NAPHTHALENE

Authors
ZOLTEWICZ JA MAIER NM FABIAN WMF
Citation
Ja. Zoltewicz et al., ATROPISOMERISM OF COFACIAL PYRIDINE RINGS - SYNTHESIS, PROTON NMR-SPECTRA AND CONFORMATIONS OF 1,8-DI(3'-PYRIDYL)NAPHTHALENE, Tetrahedron, 52(26), 1996, pp. 8703-8706
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
26
Year of publication
1996
Pages
8703 - 8706
Database
ISI
SICI code
0040-4020(1996)52:26<8703:AOCPR->2.0.ZU;2-I
Abstract
The title compound prepared by Pd-catalyzed coupling of 1,8-dibromonap hthalene and diethyl(3-pyridyl)borane shows syn-anti diastereoisomeris m due to restricted rotation at ambient temperatures. AMI and PM3 comp utations indicate the preferred T-shaped transition state for rotation has a highly deformed naphthalene ring. There is a slight preference for H4' and not the nitrogen lone electron pair to be directed at the face of the other pyridyl ring. Copyright (C) 1996 Elsevier Science Lt d