ORGANIC CHEMISTRY USING WEAKLY ELECTROPHILIC SALTS: THE REACTION WITH NITROGEN NUCLEOPHILES

摘要

The reaction of electrophilic salts, which were obtained by the treatment of acetals with TESOTf·2,4,6-collidine, with nitrogen nucleophiles was studied in detail. Treatment of the salts with potassium phthalimide afforded the corresponding N,O-acetals in good yields. The use of hydrazine in place of potassium phthalimide gave the corresponding hydrazones. The reaction is very mild and chemoselective, and acid-labile functional groups can tolerate these conditions.