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...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 22; pp. 7575 - 7584
Main Authors Anderson, Kraig K, Shultz, David A, Dougherty, Dennis A
Format Journal Article
LanguageEnglish
Published American Chemical Society 31.10.1997
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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