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15.1.1.4.4.3.1 Method 1: Addition–Elimination Reactions

DOI: 10.1055/sos-SD-015-00002

Spitzner, D.Science of Synthesis, (200515194.

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.[‌1058‌‌1060‌] 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).[‌1057‌,‌1061‌‌1064‌] 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]

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