The Intramolecular Radical Cation Induced Diels-Alder Reaction in the Diene - Diene Format

Abstract

Two 1,3,8,10-undecatetraenes were synthesized to test the viability of the intramolecular radical cation induced Diels-Alder reaction in the diene - diene format. Cyclization was successful only for the substituted tetraene with the lower oxidation potential. The major hexahydroindene product possessed a trans ring juncture demonstrating a selectivity for the endo stereochemistry.

Keywords

• Radical cation
• Diels-Alder reaction
• intramolecular cyclization