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. Author manuscript; available in PMC: 2012 Feb 2.
Published in final edited form as: J Am Chem Soc. 2010 Dec 23;133(4):949–957. doi: 10.1021/ja1081519

Scheme 1.

Scheme 1

Rate constants of cycloadditions of DIBO (2) with various 1,3-dipoles: nitrile oxide, azide, nitrone and diazocarbonyl derivatives. k’ is the relative rate with benzyl azide set at 1. The second order rate constant for nitrone 9 was determined by using equimolar mixture of reagents due to a strong absorbance at 305 nm.