Optimizing the lifetimes of phenoxonium cations derived from vitamin E via structural modifications-Reference-Cited by-同舟云学术

Optimizing the lifetimes of phenoxonium cations derived from vitamin E via structural modifications

Published:2015 Issue:48 Volume:13 Page:11732-11739
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Yue Yanni¹²³⁴⁵,Novianti Maria L.¹²³⁴⁵,Tessensohn Malcolm E.¹²³⁴⁵,Hirao Hajime¹²³⁴⁵,Webster Richard D.¹²³⁴⁵

Affiliation:

1. Division of Chemistry and Biological Chemistry

2. School of Physical and Mathematical Sciences

3. Nanyang Technological University

4. Singapore 637371

5. Singapore

Abstract

Systematic synthesis of a number of new phenolic compounds with structures similar to vitamin E led to the identification of several sterically hindered compounds that when electrochemically oxidised in acetonitrile in a –2e⁻/–H⁺ process formed phenoxonium diamagnetic cations that were resistant to hydrolysis reactions.

Funder

Institute of Chemical and Engineering Sciences

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2015/OB/C5OB01868D

Reference48 articles.

1. K. Yoshida , in Electrooxidation in Organic Chemistry: The Role of Cation Radicals as Synthetic Intermediates, Wiley, New York, 1983, pp. 174–186

2. O. Hammerich and B.Svensmark, in Organic Electrochemistry, ed. H. Lund and M. M. Baizer, Marcel Dekker, New York, 3rd edn, 1991, ch. 16

3. Syntheses via anodically produced phenoxenium ions. Applications in the field of peptides and carbohydrates