A DFT study on the thermal aryl migration in aryliodonium ylides. Support for a concerted mechanism.

J Org Chem

Laboratory of Applied Quantum Chemistry, and Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 541 24, Greece.

Published: September 2006

A DFT study on the intramolecular thermal phenyl migration in iodonium ylides supports a concerted mechanism. In contrast to the two, different than each other, suggested mechanisms, involving only intermediates, this study indicates a single-step, transition-state one--involving a five-membered cyclic ring--with no intermediates. The frontier-orbital-controlled migration also confirms the different thermal behavior of two different ylides.

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http://dx.doi.org/10.1021/jo0610964DOI Listing

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