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Spitzner, D., Science of Synthesis, (2005) 15, 194.
Relatively stable and safe 1-fluoropyridinium compounds are the starting materials for 2-substituted pyridines.[1057] The reaction with diazocarbonyl compounds or with lithium enolates gives both 2-oxygenated and 2-alkylated pyridines.[1058–1060] Sulfur nucleophiles and oxygen nucleophiles can be used in the substitution reactions of 1-fluoropyridinium compounds to obtain 2-(alkylsulfanyl)- and 2-alkoxypyridines, respectively, e.g. formation of 824 (Scheme 273).[1057,1061–1064] N,N′-Difluorobipyridinium salts, e.g. 825, are fluorinating agents that are converted into the corresponding 2-hydroxy compounds which can be easily acetylated to give the 2-acetoxy derivatives, e.g. 826 (Scheme 273).[1064]
Meeeee 888 Meeeeeee–Meeeeeeeeee Meeeeeeee ee Meeeeeeeee Meeeeeeee[8888,8888,8888]
Meeeeeeeeeeee eeeeeeeeeeee ee eee π-eeeeeeeee eeeeeeee ee eeeeee eeeeeeeee; eeeeeee, eee eeeeeeeeeeee ee eeeeeeeeeee ee eeeee eeeee 888 ee eeeeeeeeeee eee eee M—M eeee ee eee eeeeeeeeeee eeeee eeeee ee eeeeeee eeee eeee eee eeeeee eeee ee eeee eee eeeeeeeeeeeee 8-eeeeeeeeeee-8-eeeee, e.e. 888 (Meeeee 888).[8888]
References
[1057] | Meeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[1058] | Meeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[1059] | Meeeeeee, M. M.; Meeeeeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
[1060] | Meeeeeee, M. M.; Meeeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[1061] | Meeeeeee, M. M.; Meeeeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[1062] | Meeeeee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeee, M., M. Meeeeeee Meee., (8888) 88, 888. |
[1063] | Meee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[1064] | Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[1065] | Meeeee, M.; Meeeee, M.; Meeeee-Meeee, M. M.; Meeeeeeee, M. M.; Meeeeee-Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.