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. 2002 Feb 20;124(7):1130-1.
doi: 10.1021/ja016622h.

An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene

Pierluigi Caramella  1 , Paolo Quadrelli, Lucio Toma
Affiliations

An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene

Pierluigi Caramella et al. J Am Chem Soc. .

Abstract

The stereospecific endo dimerization of cyclopentadiene takes place through an asynchronous and symmetrical bispericyclic transition structure, which shows a merging of the 4+2 and 2+4 cycloaddition paths. The shape of the transition structure testifies to the presence of attractive Salem/Houk secondary orbital interactions assisting the endo approach.

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