Photo racemization of 2,2'-dihydroxy-1,1'-binaphthyl derivatives.

Chirality

Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo, Japan.

Published: February 2022

AI Article Synopsis

  • The study examined the photo racemization process of BINOL and its various ethers using circular dichroism, chiral HPLC, and energy barrier calculations.
  • BINOL underwent racemization the quickest, while its monomethyl and monobutyl ethers reacted about seven times slower.
  • The dimethyl ether showed such slow racemization rates that it couldn't be measured under the conditions tested.*

Article Abstract

Photo racemization of 2,2'-dihydroxy-1,1'-binaphthyl (BINOL) and its monomethyl ether, monobutyl ether, and dimethyl ether was studied by means of circularly dichroism spectra, chiral HPLC, and theoretical calculations of rotation energy barriers. Racemization was fastest for BINOL and about one seventh as fast for the monomethyl and monobutyl ethers while it was too slow to be detected for the dimethyl ether under the present conditions.

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Source
http://dx.doi.org/10.1002/chir.23400DOI Listing

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