BIOMAT Database Logo BIOMAT Database Logo

Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes. 2010

Craig S McKay, and Joseph Moran, and John Paul Pezacki
Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, ON, CanadaK1A 0R6.

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.

UI MeSH Term Description Entries
D009570 Nitriles Organic compounds containing the -CN radical. The concept is distinguished from CYANIDES, which denotes inorganic salts of HYDROGEN CYANIDE. Nitrile
D009589 Nitrogen Oxides Inorganic oxides that contain nitrogen. Nitrogen Oxide,Oxide, Nitrogen,Oxides, Nitrogen
D010087 Oxides Binary compounds of oxygen containing the anion O(2-). The anion combines with metals to form alkaline oxides and non-metals to form acidic oxides. Oxide
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D003516 Cycloparaffins Alicyclic hydrocarbons in which three or more of the carbon atoms in each molecule are united in a ring structure and each of the ring carbon atoms is joined to two hydrogen atoms or alkyl groups. The simplest members are cyclopropane (C3H6), cyclobutane (C4H8), cyclohexane (C6H12), and derivatives of these such as methylcyclohexane (C6H11CH3). (From Sax, et al., Hawley's Condensed Chemical Dictionary, 11th ed) Cyclic Olefins,Cycloalkanes,Cycloalkenes,Cycloalkynes,Cyclic Acetylenes,Cyclic Alkenes,Alkenes, Cyclic,Olefins, Cyclic

Related Publications

Craig S McKay, and Joseph Moran, and John Paul Pezacki
Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells.
September 2011, Chemical communications (Cambridge, England),
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Transition states of strain-promoted metal-free click chemistry: 1,3-dipolar cycloadditions of phenyl azide and cyclooctynes.
April 2008, Organic letters,
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity.
February 2011, Journal of the American Chemical Society,
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Intramolecular 1,3-dipolar cycloadditions of norbornadiene-tethered nitrones.
July 2001, The Journal of organic chemistry,
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Exploring strain-promoted 1,3-dipolar cycloadditions of end functionalized polymers.
July 2014, Chemistry (Weinheim an der Bergstrasse, Germany),
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Strain-promoted cycloadditions involving nitrones and alkynes--rapid tunable reactions for bioorthogonal labeling.
August 2014, Current opinion in chemical biology,
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Branched Polyhedral Oligomeric Silsesquioxane Nanoparticles Prepared via Strain-Promoted 1,3-Dipolar Cycloadditions.
July 2015, Langmuir : the ACS journal of surfaces and colloids,
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone.
April 2012, Organic & biomolecular chemistry,
Craig S McKay, and Joseph Moran, and John Paul Pezacki
3-Oxidopyridinium Ions Are Versatile Bioorthogonal Dipoles for Use in Cycloadditions with Cyclooctynes.
February 2024, Chemistry (Weinheim an der Bergstrasse, Germany),
Craig S McKay, and Joseph Moran, and John Paul Pezacki
Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.
June 2017, Journal of the American Chemical Society,
Copied contents to your clipboard!