1636897-01-2Relevant academic research and scientific papers
Synthesis of dihydropyrans and dihydrofurans via radical cyclization of unsaturated alcohols and 1,3-dicarbonyl compounds
Aslan, Hakan,Akpbox Drawings Light Down And Leftnar, Deniz E.,?ktemer, Atilla,Yakut, Mehtap,Alag?z, O?uzhan
, p. 652 - 663 (2014)
The oxidative cyclization reactions of 1,3-dicarbonyl compounds 1a-1c and α,β-unsaturated alcohols 2a-2f with Mn(OAc)3 were performed, leading to dihydrofurans. Treatment of 1a and 1b with 2-methylbut-3-en-2-ol (2a) gave dihydrofurans 3aa and 3ba, and dihydropyrans 4aa and 4ba, as unexpected products. While the reaction of 2-methylbut-3-yn-2-ol (2b) with acetylacetone (1b) yielded a bifuran, ethyl acetoacetate (1a) led to a mixture of furan, bifuran, and salicylate derivatives. Besides, surprisingly, styryl-substituted dihydrofurans were obtained from the reactions of 1,3-dicarbonyl compounds and (3E)-2,4-diphenylbut-3-en-2-ol. The reaction mechanisms were proposed for the formation of the different products, considering intermediates in these reaction mixtures. Copyright
