A DFT Study on Diels-Alder Reaction of Dibenzazepine and 2,5-Dimethylfuran Using Different Solvents and Temperature Conditions

Abstract

The Diels-Alder reaction involves cycloaddition of dienes and dienophiles to form a six-membered ring. The reaction involves the formation of adduct which can have two possible configurations, viz, endo and exo. For a vast majority of the Diels-Alder reactions, endo is the major adduct. This first ever study focuses on the Diels-Alder reaction between dibenzazepine and 2,5-dimethylfuran depicted by the computational method using Gaussian 16 software at different basis set levels. The formation of adduct is studied under different temperatures in the gas phase and aqueous medium. The kinetically favored endo adduct is preferred at low temperatures as compared to exo adduct. The adduct gets dehydrated further to give tribenzazepine as the final product. The applicability of the reaction is also proved experimentally in absence or presence of aqueous medium. The final product is characterized and its experimental and theoretical ¹HNMR are compared.

Keywords:

• Adduct
• Diels Alder (DA)
• tribenzazepine
• water

Disclosure statement

The authors state no conflict of interest.

Additional information

Funding

The authors would like to thank Faculty Research Grant Scheme (FRGS), Guru Gobind Singh Indraprastha University, Dwarka, New Delhi, for financial support of this project.