Abnormal Nucleophilic Substitution in 3-Trichloromethylpyridine, its N-Oxide and 3,5-Bis(trichloromethyl)pyridine

Article abstract of DOI:10.1016/0040-4020(95)00734-P

The scope of abnormal reactions of nucleophiles with β-trichloromethylazines is further explored: reactions of 3-trichloromethylpyridine with nucleophiles other than methoxide, and reactions of 3-trichloromethylpyridine N-oxide and 3,5-bis(trichloromethyl)pyridine with methoxide.Attack at a ring carbon, followed by hydrogen migration to the side-chain, occured in most cases, though attack at the trichloromethyl carbon was also sometimes observed.