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

(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 racemizat...

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Detalles Bibliográficos
Autores principales: Zhang, Zhaoming, Wang, Yue, Nakano, Tamaki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273637/
https://www.ncbi.nlm.nih.gov/pubmed/27854333
http://dx.doi.org/10.3390/molecules21111541
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author Zhang, Zhaoming
Wang, Yue
Nakano, Tamaki
author_facet Zhang, Zhaoming
Wang, Yue
Nakano, Tamaki
author_sort Zhang, Zhaoming
collection PubMed
description (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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spelling pubmed-62736372018-12-28 Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol) Zhang, Zhaoming Wang, Yue Nakano, Tamaki Molecules Communication (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. MDPI 2016-11-16 /pmc/articles/PMC6273637/ /pubmed/27854333 http://dx.doi.org/10.3390/molecules21111541 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Zhang, Zhaoming
Wang, Yue
Nakano, Tamaki
Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)
title Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)
title_full Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)
title_fullStr Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)
title_full_unstemmed Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)
title_short Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol)
title_sort photo racemization and polymerization of (r)-1,1′-bi(2-naphthol)
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273637/
https://www.ncbi.nlm.nih.gov/pubmed/27854333
http://dx.doi.org/10.3390/molecules21111541
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AT wangyue photoracemizationandpolymerizationofr11bi2naphthol
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