2589-81-3Relevant academic research and scientific papers
Self-Condensation of Enaminodiones as a Method for Benzene Ring Construction: Synthesis of Diacyl-Substituted Phenols and Catechols
Obydennov, Dmitrii L.,Chernyshova, Elena V.,Sosnovskikh, Vyacheslav Y.
, p. 6491 - 6501 (2019/05/24)
A novel transition metal-free approach for the construction of the benzene core has been developed through self-condensation of available enaminodiones. Functionalized acyl-substituted phenols and catechols were obtained in 29-97% yields with high chemoselectivity under mild conditions. This base-promoted formal [4+2] annulation proceeds via cyclohexanone formation and involves the cascade transformation based on double Michael addition and aromatization (retro-Claisen cleavage and amine elimination).
A REEXAMINATION OF THE RETRO-FRIES REARRANGEMENT OF SOME o-HYDROXYKETONES
Martin, Robert,Lafrance, Jean Ronald,Demerseman, Pierre
, p. 539 - 548 (2007/10/02)
The retro-Fries rearrangement, catalyzed by protic and Lewis acids, was studied for some o-hydroxyketones.The results are consistent with the mechanism of an heterolytic cleavage and rearrangement.It appears that, in general, Lewis acids do not induce the retro-Fries rearrangement of o-hydroxyketones.However, in certain cases, it may be brought about the presence of a protic acid generated in situ, from a solvent-catalyst interaction.
