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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

James B. Derr,

^a John A. Clark,

^b Maryann Morales,

^c Eli M. Espinoza,

‡^c Sandra Vadhin

§^b and Valentine I. Vullev

*^abcd

Author affiliations

* Corresponding authors

^a Department of Biochemistry, University of California, Riverside, CA 92521, USA
E-mail: vullev@ucr.edu

^b Department of Bioengineering, University of California, Riverside, CA 92521, USA

^c Department of Chemistry, University of California, Riverside, CA 92521, USA

^d 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.

Download options Please wait...

Supplementary files

Supplementary information PDF (4673K)

Article information

DOI: https://doi.org/10.1039/D0RA04465B
Article type: Paper
Submitted: 08 Apr 2020
Accepted: 26 May 2020
First published: 25 Jun 2020
This article is Open Access

Download Citation

RSC Adv., 2020,10, 24419-24424

Permissions

Request permissions

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

J. B. Derr, J. A. Clark, M. Morales, E. M. Espinoza, S. Vadhin and V. I. Vullev, RSC Adv., 2020, 10, 24419 DOI: 10.1039/D0RA04465B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Social activity

Fetching data from CrossRef.
This may take some time to load.

RSC Advances

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements