Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)

Author: Zhang Zhaoming   Wang Yue   Nakano Tamaki  

Publisher: MDPI

E-ISSN: 1420-3049|21|11|1541-1541

ISSN: 1420-3049

Source: Molecules, Vol.21, Iss.11, 2016-11, pp. : 1541-1541

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Abstract

(R)-1,1’-Bi(2-naphthol) ((R)-BINOL) in an acetonitrile solution lost optical activity upon irradiation with an Hg–Xe lamp. HPLC resolution of the product indicated that (R)-BINOL was racemized upon irradiation, and SEC analysis suggested that a polymeric product was formed in the course of racemization. It is proposed that polymerization of BINOL can occur before it is racemized and that a unit in a polymer derived from BINOL may lose its optical activity afterwards due to in-chain racemization and/or reduction. The polymeric products seem to consist not only of BINOL residues but also of residues derived from acetonitrile as well as those derived through reduction of BINOL.

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