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pseudopericyclic

A concerted transformation is pseudopericyclic if the primary changes in bonding occur within a cyclic array of atoms at one (or more) of which nonbonding and bonding atomic orbitals interchange roles. A formal example is the enol → enol prototropy of pentane-2,4-dione (acetylacetone).
P04932
Because the π- and σ-atomic orbitals that interchange roles are orthogonal, such a reaction does not proceed through a fully conjugated transition state and is thus not a pericyclic reaction and therefore not governed by the rules that express orbital symmetry restrictions applicable to pericyclic reactions.
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1154
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.P04932.
Original PDF version: http://www.iupac.org/goldbook/P04932.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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