46398-15-6Relevant academic research and scientific papers
ENAMINE CHEMISTRY. PART 39. MULTIPATH REACTION OF METHYL VINYL KETONE WITH DIENAMINES OF 5-OXO-Δ1,8a-2-OCTALONES, 1,2,3,6,7,8a-HEXAHYDROINDEN-5-ONE, AND ISOPHORONE
Hickmott, Peter W,Simpson, Richard
, p. 2447 - 2475 (2007/10/02)
Reaction of methyl vinyl ketone (MVK) with dienamines of cyclic α,β-unsaturated ketones has been further studied.The polydentate reactivity of the reagents results in multipath reactions leading to complex mixtures.In every case the main product obtained using toluene as solvent was that derived by cycloaddition across the β',γ-positions of the dienamine. β,δ-Annulation followed by aromatization also occurred with dienamines from 5-oxo-Δ1,8a-2-octalones and 1,2,3,6,7,8a-hexahydroinden-5-one.No β,δ-annulation was observed with the isophorone dienamine.Instead reaction with MVK gave β- and δ-alkylation products and α,β'-annulation.Those reactions studied in methanol as solvent resulted in reduced cycloaddition and increased β,δ-annulation, or β-alkylation in the case of isophorone.Possible reasons for the diverse nature of the product mixtures and the NMR and stereochemical assignments of the cycloaddition products are discussed.
