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Synthesis and Resolution of the Atropisomeric 1,1'-Bi-2-naphthol: An Experiment in Organic Synthesis and 2-D NMR Spectroscopy

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Kendrew K. W. Mak

Department of Chemistry, The Chinese Univeristy of Hong Kong, Shatin, Hong Kong, P. R. China

J. Chem. Educ., 2004, 81 (11), p 1636

DOI: 10.1021/ed081p1636

Publication Date (Web): November 1, 2004

Section:

History, Education, and Documentation

Abstract

The synthesis and resolution of the atropisomeric 1,1'-bi-2-naphthol illustrates several important concepts in organic chemistry and serves as a good experiment for organic chemistry laboratory course of intermediate to advanced levels. Racemic 1,1'-bi-2-naphthol is synthesized by the oxidative coupling of 2-naphthol and is resolved into the enantiopure form by the selective inclusion compound formation of the R enantiomer with (â’)-N-benzylcinchonidinium chloride. The enantiomeric excess of the products are determined by chiral HPLC. The naphthol unit of 1,1'-bi-2-naphthol is composed of a benzene and a phenol fused together. Both ¹H and ¹³C NMR spectra show complicated and overlapping signals in the aromatic region and complete signal assignment is extremely difficult. Unambiguous signal assignment is made possible with the help of various 2-D NMR techniques such as COSY, HMQC, and COLOC. It serves as an advanced exercise for spectroscopic structural identification of organic compounds.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Chromatography

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