Abstract
This chapter introduces perturbational molecular orbital theory using the Salem–Klopman equation. For cycloadditions, the equation is simplified to a frontier orbital expression and this is applied to predict and rationalize the features of reactivity, regioselectivity and periselectivity. The Diels–Alder reaction with different substitution patterns of the reacting components has been dealt with in respect of its frontier orbital control and ‘ortho/para’ selectivity. The features of site selectivity, Lewis acid catalysis and regiochemical preference of hetero Diels–Alder reaction, Diels–Alder/retro-Diels–Alder sequence as a synthetic strategy and dehydro-Diels–Alder reactions are also described. The 1,3-dipolar cycloadditions and their regioselectivity using frontier orbital analysis are presented taking a variety of 1,3-dipoles employed for heterocyclic synthesis. A brief description of diyl cycloadditions using trimethylenemethane is included. The periselectivity in cycloadditions including fulvene cycloadditions has been analyzed using frontier orbital theory. Finally two useful cycloadditions involving singlet oxygen and ozone are described.
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