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Attempted Synthesis of a Stable, Quintet, Tetraphenoxyl Tetraradical: Facile Rearrangement of a Substituted Bicyclobutane
journal contribution
posted on 1997-10-31, 00:00 authored by Kraig K. Anderson, David A. Shultz, Dennis A. DoughertyThe preparation of tetraphenol 3 and its
attempted oxidation to tetraradical 2 are
described.
Tetraphenoxyl 2 was envisioned as a more stable analog
of the previously reported, quintet
tetraradical 1. However, EPR studies on 3
and model compounds and crystallographic characterization of the product from oxidation of 3 suggest that
2 is not a viable target. Apparently, 2 or
an
intermediate in the multistep oxidation path leading to it undergoes a
ring closure to a bicyclobutane.
The bicyclobutane, in turn, undergoes a surprisingly facile
rearrangement to the analogous
butadiene structure.