(3+2)-Cycloaddition Reactions of Oxyallyl Cations
نویسندگان
چکیده
منابع مشابه
Quantum chemical characterization of cycloaddition reactions between 1,3-butadiene and oxyallyl cations of varying electrophilicity†
Hydroxyallyl cation and lithium and sodium oxyallyl cations are predicted to react with 1,3-butadiene both in a stepwise fashion and via concerted [4 3] cycloaddition with so-called extended stereochemistry. With hydroxyallyl cation, the stepwise process is preferred and subsequent second bond closures generate products equivalent to those that would arise from concerted [4 3] or [3 2] cyclo...
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The reaction of a series of allyl-substituted bis(phenylsulfony1)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)l13-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene and subsequent PhS02elimination to give the phenylsulfonyl substituted allene. Th...
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Cycloaddition reactions between 1,3-butadiene and the C-terminated SiC(1 0 0)-c(2 · 2) surface have been addressed using quantum-chemical methods. The c(2 · 2) structure consists of ACBCA bridges between underlayer Si atoms which themselves form SiASi bonds. Of various possible reaction products, the one formed by a [2+ 4] reaction with the ACBCA bridge (giving a species resembling 1,4-cyclohex...
متن کاملTheoretical studies on cycloaddition reactions
Cycloaddition reactions represent one of the most powerful processes in organic chemistry. The most common types of cycloaddition reactions are the Diels-Alder (DA) and the 1,3-dipolar cycloaddition reactions (1,3-DCs) which lead to five and six membered rings, respectively. In our ongoing efforts to contribute to the understanding of DA and 1,3-DCs; we studied the following using the B3LYP/6-3...
متن کاملStereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides.
The first intramolecular [4 + 3] cycloaddition reaction using nitrogen-stabilized chiral oxyallyl cations that are tethered to furan or diene through the nitrogen atom is described here. Formation of these nitrogen-stabilized chiral oxyallyl cations is achieved by a chemoselective epoxidation of chiral allenamides via syringe pump addition of dimethyl dioxirane. The ensuing cycloaddition can be...
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ژورنال
عنوان ژورنال: Synthesis
سال: 2014
ISSN: 0039-7881,1437-210X
DOI: 10.1055/s-0034-1378918