The reaction of azo-bis-cyanuric chloride as strong electrophilic aza-dienophile in Diels-Alder cycloaddition with a number of dienes of different nucleophilicity, namely 2,3-dimethylbutadiene, 2-methylbutadiene and 1-acethoxybutadiene, was carried out and computationally analyzed on B3LYP/6-31G(d,p) level. Local and global reactivity indices, based on FMO theory, as well as TS geometries and activation energies were calculated. Reaction proceeds rapidly with high yields and in mild conditions. Ways of products further modification by chlorine atoms substitution were also studied.
The Diels-Alder reaction is widely used in organic synthesis, since it allows using a variety of dienes and dienophiles to obatin six-membered cycles in one step. Azo compounds, especially with electron deficient substituents, such as the 1,3,5-triazine ring, can interact as active dienophiles in the Diels-Alder reactions.