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Communication | Special issue | Vol 37, No. 3, 1994, pp.1463-1466
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S155
Photolytic Generation of N-Acylnitrenium Ions under Neutral Conditions: Synthesis of Polycyclic Lactams

Rudolph A. Abramovitch* and Qing Shi

*Department of Chemistry, Clemson University, Clemson, SC 29631, U. S. A.


Intramolecular electrophilic aromatic acylamination has been achieved by the photolysis of N-aroylaminopyridinium tetrafluoroborates under neutral conditions. Acylnitrenium ions were most likely generated which substituted the adjacent ring without undergoing Curtius-type rearrangement.