Communication
[1,3], [3,3], and [3,5] Sigmatropic Rearrangements of Esters Are Pseudopericyclic
First published: 04 February 2004
Citations: 83
Abstract
Allowed by orbital symmetry rules, the [3,5] sigmatropic ester rearrangement of ester 1 even has a lower barrier than a competing [3,3] rearrangement, according to ab initio calculations. This surprising result is a consequence of the lack of orbital overlap in the pseudopericyclic transition state.
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