DFT study on the mechanism of the cycloaddition reaction of azaheptafulvene withfulvene

The cycloaddition reactions of fulvene with azaheptafulvene have been investigated using densityfunctional theory (DFT)-based reactivity indices and activation energy calculations at the M۰۶-۲X/cc-pVDZ levelof theory. Two modes of [۴+۶] and [۴+۲] cycloaddition reactions can occur from the results of Diels-Alderreactions of fulvene with azaheptafulvene. The energy results indicated that the [۶+۴] cycloaddition reaction ismore favorable than [۴+۲] cycloaddition reaction. The reactions take place via an asynchronous one-stepmechanism with a polar character, and an analysis of the conceptual DFT indices explains the polar character ofthese reactions. which proceeds through a two-stage one-step mechanism.

کلیدواژه ها:

Diels-Alder ، DFT method ، fulvene and azaheptafulvene ، regioselectivity ، Reactivity indices