Atropisomerism of cofacial pyridine rings. Synthesis, proton NMR spectra and conformations of 1,8-di(3′-pyridyl)naphthalene
1996; Elsevier BV; Volume: 52; Issue: 26 Linguagem: Inglês
10.1016/0040-4020(96)00447-4
ISSN1464-5416
AutoresJohn A. Zoltewicz, Norbert M. Maier, Walter M. F. Fabian,
Tópico(s)Advanced NMR Techniques and Applications
ResumoThe title compound prepared by Pd-catalyzed coupling of 1,8-dibromonaphthalene and diethyl(3-pyridyl)borane shows syn-anti diastereoisomerism due to restricted rotation at ambient temperatures. AM1 and PM3 computations 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.
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