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Paper | Special issue | Vol 74, No. 1, 2007, pp.273-281
Published online, 8th June, 2007
DOI: 10.3987/COM-07-S(W)4
Intramolecular Benzylic Cyclization with Nitrenium Ions Generated from N-Acylaminophthalimides Using Phenyliodine(III) Bis(trifluoroacetate): Formation of Phenyl Substituted Lactams

Akira Nagashima, Takeshi Sakamoto, and Yasuo Kikugawa*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

N-Phthalimido-N-acylnitrenium ions generated from N-acylaminophthalimides using phenyliodine(III) bis(trifluoroacetate) in polyfluoro alcohols do not undergo intramolecular aromatic substitution reactions. Instead, intramolecular cyclization to the benzylic position occurs to afford lactams having a phenyl group substituted at the α-position to the ring nitrogen. These reactions proceed in moderate to good yields.