posted on 2006-09-01, 00:00authored byEvangelos G. Bakalbassis, Spyros Spyroudis, Elizabeth Tsiotra
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 oneinvolving a five-membered cyclic ringwith no intermediates. The frontier-orbital-controlled migration also confirms the different
thermal behavior of two different ylides.