Aqueous-Phase Deactivation and Intramolecular [2 + 2 + 2] Cycloaddition of Oxanorbornadiene Esters

Abstract

Both inter- and intramolecular degradation pathways were identified for the aqueous phase deactivation of oxanorbornadiene (OND) electrophiles, and propargylic OND esters were found to undergo facile intramolecular [2 + 2 + 2] homo-Diels-Alder cycloaddition in polar media.