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Note | Special issue | Vol 79, No. 1, 2009, pp.1113-1120
Published online, 9th December, 2008
DOI: 10.3987/COM-08-S(D)69
Organic Chemistry Using Weakly Electrophilic Salts: The Reaction with Nitrogen Nucleophiles

Hiromichi Fujioka,* Ozora Kubo, Kento Senami, Kazuhisa Okamoto, Takashi Okitsu, and Yasuyuki Kita*

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan

Abstract

The reaction of electrophilc salts, which were obtained by the treatment of acetals with TESOTf2,4,6-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.