Regio- and stereoisomeric composition of the product mixture in the Diels–Alder reaction of dicyclopentadiene with bicyclononadiene: a NMR and DFT quantum chemical investigation

Abstract

The regio- and stereoisomeric composition of the product mixture in the Diels–Alder reaction between dicyclopentadiene and bicyclononadiene is determined by 2D 1H–13C HMQC and HMBC and 1H 2D DQF COSY and NOESY NMR techniques. The absence in the experimental mixture of one of the expected products is explained by high-level quantum chemical density functional theory calculations.