Intramolecular photoaddition reactions of (aminoalkyl)styrylamides

Frederick D. Lewis*, Jill M. Wagner-Brennan, John M. Denari

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The photochemical reactions of a family of styrene-spacer-amine -molecules in which the spacer consists of a rigid amide group in the middle of a flexible alkane chain have been investigated. Our study of the photophysics of these molecules has shown that the amide linker can facilitate intramolecular styrene-amine exciplex formation (J. Phys. Chem., in press). We report here the photochemical behavior of these amide-linked (aminoalkyl)styrylamides. Several tertiary amines are found to undergo regioselective α-C-H addition to the styrene double bond resulting in the formation of medium-ring lactams. A secondary amine undergoes N-H addition yielding an azalactam. The dependence of these reactions upon spacer structure, amine and amide substitution, and solvent polarity is discussed.

Original languageEnglish (US)
Pages (from-to)139-143
Number of pages5
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume112
Issue number2-3
DOIs
StatePublished - Jan 31 1998

Keywords

  • (Aminoalkyl)styrylamide
  • Lactams
  • Photochemical synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

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