100421-99-6Relevant academic research and scientific papers
The Formation of Ozonides by Electron Transfer Induced Photo-oxidation of Small-ring Cycloalkenes
Kirschenheuter, Gary P.,Griffin, Gary W.
, p. 596 - 597 (1983)
Several polymethyl-1,2-diphenylcyclobutenes have been subjected to photo-oxidation in acetonitrile in the presence of 9,10-dicyanoanthracene and it is possible to isolate the corresponding ozonides, in moderate yields (ca. 13percent), apparently formed from oxirans produced in a primary step; 1,4-diketones are not generated from the ozonides under the reaction conditions although they are formed as reaction products by what must be an alternative mechanism.
THE SENSITIZED PHOTOOXYGENATION OF METHYL SUBSTITUTED 1,2-DIPHENYLCYCLOBUTENES
Griffin, Gary W.,Kirschenheuter, Gary P.,Vaz, Caetan,Umrigar, Pesi P.,Lankin, David C.,Christensen, Siegfried
, p. 2069 - 2080 (2007/10/02)
A series of Me substituted 1,2-diphenylcyclobutenes was subjected to dye-sensitized photooxidation in the presence of methylene blue.In the case of the 3,3-dimethyl-, 3,3,4-trimethyl- and 3,3,4,4-tetramethyl-1,2-diphenylcyclobutenes, the sensitized oxidations are accompanied by ring-contraction with concomitant ortho hydroxylation of one aromatic nucleus.When electron transfer induced photooxidation techniques utilizing 9,10-dicyanoanthracene (DCA) as a sensitizer are employed with the series of Me substituted diphenylcyclobutenes, the reactions take a markedly different course and a broad spectrum of oxidation products are obtained including, most notably, ozonides of the cyclobutenes.The mechanisms of these conversions are addressed and the significance of the results discussed.
