Topic
Methyl vinyl ketone
About: Methyl vinyl ketone is a research topic. Over the lifetime, 1510 publications have been published within this topic receiving 26839 citations. The topic is also known as: 3-buten-2-one & gamma-oxo-alpha-butylene.
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TL;DR: In this article, the Sharpless asymmetric dihydroxylation and conjugated addition of acetonides to the respective unsaturated ketones were used to obtain exo-isobrevicomin (1) and exobrevicomin (2).
Abstract: (-)-exo-Isobrevicomin (1) and (+)-exo-brevicomin (2) are volatile substances produced by males of the beetles Dendroctonus ponderosae, which inhabit pine trees found in the northern hemisphere, frequently causing the death of their host. In order to obtain these aggregation pheromones, which present the 6,8-dioxabicyclo[3.2.1]octane structure, the synthetic strategies utilized in this work had as key steps the Sharpless asymmetric dihydroxylation and the conjugated addition, promoted by the Zn(Cu) couple in aqueous medium and accelerated by ultrasound. The conjugated addition of acetonides 13 and 14 to the respective unsaturated ketones (methyl vinyl ketone and ethyl vinyl ketone) furnished the adducts 15 and 16. The intramolecular catalyzed cyclization of compounds 15 and 16 with phosphotungstic acid (H3PW12O40) produced exo-isobrevicomin (1) and exo-brevicomin (2).
18 citations
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TL;DR: In this article, the reactivities of styrene, methyl acrylate, methyl methacrylate and methyl isopropenyl ketone towards the 1-phenylethyl radical at 100° have been compared using acenaphthylene as the reference monomer.
18 citations
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TL;DR: In this paper, 2-Arnino-4,5-dihydro-3-thiophenecarbonitriles 1a-c reacted with α,β-unsaturated ketones (e.g. methyl vinyl ketone 2 and benzalacetone 3) in the presence of titanium(IV) chloride to give the corresponding Michael adducts.
17 citations
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TL;DR: The Michael addition of a β,β-dimethyl substituted silyl ketene acetal [Me2CC(OMe)OSiMe3] to α-β-unsaturated ketones, namely, 2-cyclopentenone, 2cyclohexenone and isophorone, methyl vinyl ketone and mesityl oxide occurs smoothly in the presence of the nucleophilic catalyst, tetra-n-butyl ammonium bibenzoate (TBABB) in THF giving the corresponding 1,4
17 citations
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TL;DR: In this paper, a 6-endo-oxypalladation of the triple bond is followed by a C-C coupling to give structurally diverse isochromenimines and related heterosubstituted derivatives, in which the α,β-unsaturated carbonyl moiety is incorporated as an alkyl-type exocyclic side chain.
17 citations