Dendritic Diels-Alder reactions of orange

CHED 552

Nora Ellen Hunter, hunter.29@wright.edu and William A. Feld, william.feld@wright.edu. Department of Chemistry, Wright State University, 3640 Colonel Glenn Hwy, Dayton, OH 45435
It is well known that 2,5-dicarboethoxy-3,4-diphenylcyclopentadienone undergoes Diels-Alder reactions with a variety of alkynes to produce aromatic diesters. This reaction has been extended to include multivalent alkyne derivatives made available by “Click” chemistry. For example, 1,7-octadiyne provides an alkyl tethered bis-terephthalate, and tripropargylamine I provides the tris-terephthalate. Reaction of pentaerythritol tetra-propargyl ether II provides a mixture of products. These compounds were isolated and purified by recrystallization and structurally analyzed by proton and carbon NMR.