An expeditious entry to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO): another highly active organocatalyst for oxidation of alcohols

Masatoshi Shibuya; Masaki Tomizawa; Yusuke Sasano; Yoshiharu Iwabuchi

doi:10.1021/jo900486w

An expeditious entry to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO): another highly active organocatalyst for oxidation of alcohols

J Org Chem. 2009 Jun 19;74(12):4619-22. doi: 10.1021/jo900486w.

Authors

Masatoshi Shibuya¹, Masaki Tomizawa, Yusuke Sasano, Yoshiharu Iwabuchi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan.

PMID: 19476345
DOI: 10.1021/jo900486w

Abstract

A practical, three-step synthetic route to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO, 3), an unhindered, stable class of nitroxyl radical, has been developed. ABNO exhibits a highly active nature compared with TEMPO in the catalytic oxidation of alcohols to their corresponding carbonyl compounds.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Azabicyclo Compounds / chemical synthesis*
Catalysis
Cyclic N-Oxides / chemistry
Cyclization
Free Radicals / chemical synthesis
Free Radicals / chemistry
Nitrogen Oxides / chemical synthesis*
Nitrogen Oxides / chemistry
Oxidation-Reduction

Substances

Alcohols
Azabicyclo Compounds
Cyclic N-Oxides
Free Radicals
Nitrogen Oxides
nitroxyl
TEMPO