Solvent-induced selectivity of Williamson etherification in the pursuit of amides resistant against oxidative degradation

James B Derr; John A Clark; Maryann Morales; Eli M Espinoza; Sandra Vadhin; Valentine I Vullev

doi:10.1039/d0ra04465b

Solvent-induced selectivity of Williamson etherification in the pursuit of amides resistant against oxidative degradation

RSC Adv. 2020 Jun 25;10(41):24419-24424. doi: 10.1039/d0ra04465b. eCollection 2020 Jun 24.

Authors

James B Derr¹, John A Clark², Maryann Morales³, Eli M Espinoza³, Sandra Vadhin², Valentine I Vullev^{1

2

3

4}

Affiliations

¹ Department of Biochemistry, University of California Riverside CA 92521 USA vullev@ucr.edu.
² Department of Bioengineering, University of California Riverside CA 92521 USA.
³ Department of Chemistry, University of California Riverside CA 92521 USA.
⁴ Materials Science and Engineering Program, University of California Riverside CA 92521 USA.

Abstract

This article reports two discoveries. (1) 2-Methoxyethanol induces unprecedented selectivity for etherification of 5-hydroxy-2-nitrobenzic acids without forming undesired esters. (2) Such compounds are precursors for amides showing unusual robustness against oxidative degradation, essential for molecular electrets that transfer strongly oxidizing holes at about -6.4 eV vs. vacuum.