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Syntheses of compounds required as substrates for reactions with nucleophiles are reported: 2-trichloromethylquinoxaline 5, 3-trichloromethylquinoline 6, 3,5-bis(trichloromethyl)pyridine 7, 2,5-bis(trichloromethyl)pyrazine 8 and 5-trichloromethylpyrimidine 9.
The scope of abnormal reactions of nucleophiles with beta-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, occurred in most cases, though attack at the trichloromethyl carbon was also sometimes observed.