60428-18-4Relevant academic research and scientific papers
Steric and electronic effects on the Weiss reaction. Isolation of 1:1 adducts
Van Ornum, Scott G.,Li, Jin,Kubiak, Greg G.,Cook, James M.
, p. 3471 - 3478 (1997)
The mechanism of the Weiss reaction has been studied with respect to the intermediacy of 4-hydroxycyclopent-2-en-1-ones (1:1 adducts) in this process. Analysis of these experiments provides additional evidence that 4-hydroxycyclopentenones are indeed key intermediates in the Weiss reaction. Based on the reaction of dimethyl 3-oxoglutarate with benzil, pyridil, thenil, furil and phenanthrenequinone, steric effects play the major role in the overall success of this condensation to provide substituted cis-bicyclo[3.3.0]octane-3,7-diones. Moreover a trihydroxyindene [5.6] system (see 26) has been isolated for the first time under the Weiss conditions which provides additional support for the existence of cyclopentenone intermediates in this process.
