TY - JOUR
T1 - Intramolecular photoaddition reactions of (aminoalkyl)styrylamides
AU - Lewis, Frederick D.
AU - Wagner-Brennan, Jill M.
AU - Denari, John M.
N1 - Funding Information:
Financial support for this research has been provided by the National Science Foundation.
PY - 1998/1/31
Y1 - 1998/1/31
N2 - 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.
AB - 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.
KW - (Aminoalkyl)styrylamide
KW - Lactams
KW - Photochemical synthesis
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U2 - 10.1016/S1010-6030(97)00299-2
DO - 10.1016/S1010-6030(97)00299-2
M3 - Article
AN - SCOPUS:0032583655
SN - 1010-6030
VL - 112
SP - 139
EP - 143
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
IS - 2-3
ER -