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The regiospecific dimerization of methacrolein takes place through a very asynchronous and symmetrical transition structure, which shows a merging of the 4+2 and 2+4 cycloaddition paths. The geometrical features of the transition structures correspond well to a case of diradical formation. A cage of secondary orbital interactions restricts the flexibility of the diradical transition structure and...
Non-classical (bridging) and classical (Woodward-Hoffmann) secondary orbital interactions as well as a favourable electrostatic interaction are involved in the stabilization of the two lowest transition passes of the acrolein dimerization. The heteroatoms provide anchimeric assistance to the hetero Diels-Alder reaction through a neighbouring-group mechanism.
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