Ring expansion of indanyl and 1,2,3,4-tetrahydronaphthalenyl derivatives

CHED 314

Eric J. Kantorowski, ekantoro@calpoly.edu, Jessica Lee, Lauren Ross, Chris Sanborn, Jon Hopper, and Dylan Turner. Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Ave, San Luis Obispo, CA 93407
The viability of performing a radical-mediated ring expansion on the indanyl and 1,2,3,4-tetrahydronaphthalenyl rings will be described. Fusing a cyclopropylcarbinyl radical group onto the non-aromatic portion of these rings presents a bifurcated pathway that can lead either to expansion or non-expansion. Ring size (indanyl vs 1,2,3,4-tetrahydronaphthalenyl), as well as the orientation of these rings to the cyclopropylcarbinyl radical group, influences the direction that the cyclopropylcarbinyl radical will fragment. Thermokinetic data for these systems will be presented.