4.1 Article

Synthesis of 5-Metalla-Spiro[4.5]Heterodecenes by [1,4]-Cycloaddition Reaction of Group 13 Diyls with 1,2-Diketones

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CHEMISTRY-SWITZERLAND
卷 5, 期 2, 页码 948-964

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MDPI
DOI: 10.3390/chemistry5020064

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group 13 diyls; low-valent metal; cycloaddition; aldol addition

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Monovalent group 13 diyls are used as versatile reagents in oxidative addition reactions, and the [1,4]-cycloaddition reactions of these diyls with various 1,2-diketones are reported here. These reactions result in the formation of different compounds, and additional reactions with other compounds such as aldehydes and benzene rings were also studied.
Monovalent group 13 diyls are versatile reagents in oxidative addition reactions. We report here [1,4]-cycloaddition reactions of & beta;-diketiminate-substituted diyls LM (M = Al, Ga, In, Tl; L = HC[C(Me)NDipp](2), Dipp = 2,6-(Pr2C6H3)-Pr-i) with various 1,2-diketones to give 5-metalla-spiro[4.5]heterodecenes 1, 4-6, and 8-10, respectively. In contrast, the reaction of LTl with acenaphthenequinone gave the [2,3]-cycloaddition product 7, with Tl remaining in the +1 oxidation state. Compound 1 also reacted with a second equivalent of butanedione as well as with benzaldehyde in aldol-type addition reactions to the corresponding & alpha;,& beta;-hydroxyketones 2 and 3, while a reductive activation of a benzene ring was observed in the reaction of benzil with two equivalents of LAl to give the 1,4-aluminacyclohex-2,4-dien 12. In addition, the reaction of L'BCl2 (L = HC[C(Me)NC6F5](2)) with one equivalent of benzil in the presence of KC8 gave the corresponding 5-bora-spiro[4.5]heterodecene 13, whereas the hydroboration reaction of butanedione with L'BH2 (14), which was obtained from the reaction of L'BCl2 with L-selectride, failed to give the saturated 5-bora-spiro[4.5]heterodecane.

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