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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

Table 2.

One-pot oxime formation and SPANOC with DIBO (2)

graphic file with name nihms260731t2.jpg
Entry R k (M-1 s-1)a, b, c Yield (%)d
1 C6H5 (6a) 3.44 ± 0.03 55
2 2-Me-C6H4 (6g) 3.20 ± 0.03 51
3 C6H5-CH2CH2 (6h) 1.38 ± 0.01 90
a

Rate constant was determined from isolated oximes;

b

Second order rate constants were determined from pseudo first order rate constants at various concentration of nitrile oxides at 25 ± 0.1°C.

c

Pseudo first order kinetics were determined using UV-Vis spectroscopy following the decay of the absorbance of 2 at 305 nm; [2] = 6.0 × 10-5 M; for details on the concentrations of nitrile oxides, see supporting information.

d

Isolated yields of combined isomers.