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 language | English (US) |
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Pages (from-to) | 139-143 |
Number of pages | 5 |
Journal | Journal of Photochemistry and Photobiology A: Chemistry |
Volume | 112 |
Issue number | 2-3 |
DOIs | |
State | Published - Jan 31 1998 |
Funding
Financial support for this research has been provided by the National Science Foundation.
Keywords
- (Aminoalkyl)styrylamide
- Lactams
- Photochemical synthesis
ASJC Scopus subject areas
- General Chemistry
- General Chemical Engineering
- General Physics and Astronomy