Attempted Synthesis of a Stable, Quintet, Tetraphenoxyl Tetraradical: Facile Rearrangement of a Substituted Bicyclobutane
The 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...
Saved in:
Published in | Journal of organic chemistry Vol. 62; no. 22; pp. 7575 - 7584 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
31.10.1997
|
Online Access | Get full text |
Cover
Loading…
Summary: | The 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. |
---|---|
Bibliography: | ark:/67375/TPS-XT67FVQN-6 istex:D7CE4FEC70A895B70507ECD73EBC6FDBF2EC44E7 Abstract published in Advance ACS Abstracts, October 1, 1997. |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo970614v |