Exploring 1,2,3-cyclohexatriene reactivity with furan derivatives: insights into structural and electronic factors

1,2,3-Cyclohexatriene is highly reactive compound which is relatively underexplored compound, demonstrates significant potential for cycloaddition reactions. In this work, we explore the electronic structure effects of various substitutions on 1,2,3-cyclohexatriene and investigate the reaction mechanisms involving these substituted trienes using the density functional theory (DFT). The detailed analysis of global hardness, Fukui functions analysis are performed for various substituted trienes. The present study shows that increasing the bulkiness of the substituents reduces the strain in cyclohexatriene. A systematic investigation of the reactions of 1,2,3-cyclohexatriene and its substituted analogues with furan and its derivatives reveals that, despite the reduction in strain, substitution leads to an increase in the cycloaddition barrier height. This increase in the barrier is attributed to enhanced steric crowding in the transition state.