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Stereoselective Synthesis of Polysubstituted Conjugated Dienes Enabled by Photo-driven Sequential Sigmatropic Rearrangement.

Angewandte Chemie
We here report a highly stereoselective method for the synthesis of polysubstituted conjugated dienes from α-aryl α-diazo alkynyl ketones and pyrazole-substituted unsymmetric aminals under mild conditions, which was driven by photo and involved 1,6 ...
Xin Ji   +8 more
semanticscholar   +1 more source

Facile [3,3]-sigmatropic rearrangement in the reaction of ?-chloroperfluorostyrene with allyl alcohol

Bulletin of the Russian Academy of Sciences Division of Chemical Science, 1992
The reaction of α-chloroperfluorostyrene (1) with allyl alcohol in the presence of KOH at 45–50°C leads to a mixture of the allyl 2-pentafluorophenyl-2-chloro-4-pentenoate (2) and the product of the addition of the starting reagents (3). Ester2 is formed as the result of a mild [3,3]-sigmatropic rearrangement of the reaction intermediate.
V. G. Andreev   +3 more
openaire   +2 more sources

[3,3]-sigmatropic rearrangement in reaction of 2-methylthiopentafluoropropene with allyl alcohol

Journal of Fluorine Chemistry, 1991
Abstract The interaction of 2-methylthiopentafluoropropene with allyl alcohol in the conditions of paper [1] gives a mixture of the addition product (1) and the ester (2). The latter is formed as a result of [3,3]-sigmatropic rearrangement of intermediate - the fluorocarbanion (A).
V. G. Andreev   +3 more
openaire   +2 more sources

Successive Michael reaction-sigmatropic rearrangement of polyquinones with silyl ketene acetals

The Journal of Organic Chemistry, 1989
AbstractMichael type reaction of the quinizarinequinone (I) and the naphthodiquinone (IX) with (trimethylsilyloxy)furan (II) or the O‐silylated ketene acetal (V) yields the adducts (III), (VI), and (X).
Mariko Aso   +2 more
openaire   +3 more sources

Stereocontrolled Microwave-Assisted Domino [3,3]-Sigmatropic Reactions: A Winstein-Overman Rearrangement for the Formation of Differentiated Contiguous C-N Bonds.

Organic Letters, 2020
A domino [3,3]-sigmatropic rearrangement sequence employing a sequential reversible allylic azide rearrangement followed by an irreversible Overman reaction provides a new route to the formation of two contiguous C-N bonds.
Andy A Tjeng   +2 more
semanticscholar   +1 more source

Sigmatropic Rearrangements of Hypervalent-Iodine-Tethered Intermediates for the Synthesis of Biaryls.

Angewandte Chemie, 2018
Metal-free dehydrogenative couplings of aryliodanes with phenols to afford 2-hydroxy-2'-iodobiaryls have been developed. This reaction proceeds through ligand exchange on the hypervalent iodine atom followed by a [3,3] sigmatropic rearrangement and with ...
Mitsuki Hori   +5 more
semanticscholar   +1 more source

Competing Diels–Alder reactions of activated nitroethylene derivatives and [3,3]-sigmatropic rearrangements of the cycloadducts

Chemical Communications, 2002
AbstractFor Abstract see ChemInform Abstract in Full Text.
James K. Murray   +3 more
openaire   +4 more sources

Sigmatropic Reactions in Carbanions. II. The Rearrangement of Allylic Ammonium Ylides

Helvetica Chimica Acta, 1972
AbstractTwo representative cases of the [2, 3] sigmatropic rearrangement are described, and the mechanism of this reaction is discussed.
openaire   +2 more sources

An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]-Sigmatropic Rearrangement.

Angewandte Chemie, 2017
A general, asymmetric redox arylation of ynamides and thioalkynes with chiral sulfoxides is reported. This is the first example of a general 1,4-chirality transfer from sulfur to a carbon stereocenter through a sulfonium [3,3]-sigmatropic rearrangement ...
D. Kaldre   +5 more
semanticscholar   +1 more source

Transition Metal Intervention for a Classic Reaction: Assessing the Feasibility of Nickel(0)-Promoted [1,3] Sigmatropic Shifts of Bicyclo[3.2.0]hept-2-enes

, 2010
Density functional theory calculations (B3LYP/LANL2DZ) were used to evaluate the feasibility of Ni(0)-N-heterocyclic carbene-promoted [1,3] sigmatropic rearrangements of bicyclo[3.2.0]hept-2-enes to bicyclo[2.2.1]hept-2-enes.
O. Gutierrez, D. Tantillo
semanticscholar   +1 more source

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