Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes

Craig S McKay; Joseph Moran; John Paul Pezacki

doi:10.1039/b921630h

Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes

Chem Commun (Camb). 2010 Feb 14;46(6):931-3. doi: 10.1039/b921630h. Epub 2009 Dec 23.

Authors

Craig S McKay¹, Joseph Moran, John Paul Pezacki

Affiliation

¹ Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, ON, CanadaK1A 0R6.

PMID: 20107654
DOI: 10.1039/b921630h

Abstract

Strain-promoted cycloadditions of nitrones with cyclooctynes (k(2) = 1.5 M(-1) s(-1) at 25 degrees C) are up to 25 times more rapid than comparable reactions of azides.

MeSH terms

Cyclization
Cycloparaffins / chemistry*
Nitriles / chemistry
Nitrogen Oxides / chemistry*
Oxides / chemistry

Substances

Cycloparaffins
Nitriles
Nitrogen Oxides
Oxides
nitrones