Table 2.
Bimolecular rate constants (k, L·mol–1·s–1) measured for the reaction of 4-methyl-3-phenylsydnone and various acetylenes in p-cymene at 140 °C [54].
dipolarophile (disubstituted alkyne) |
105k (L·mol−1·s−1) |
dipolarophile (monosubstituted alkyne) |
105k (L·mol−1·s−1) |
MeOOC–C≡C–COOMe | 2 580 | H–C≡C–COOMe | 823 |
Ph–C≡C–COPh | 135 | H–C≡C–CH(OPr)2 | 39 |
Ph–C≡C–COOEt | 99 | H–C≡C–Ph | 18 |
Ph–C≡C–Ph | 3.0a | H–C≡C–(CH2)11CH3 | 6.0 |
Ph–C≡C–Me | 1.9 |
aIn decaline.