A non-Woodward and Hoffmann reaction path for photochemical sigmatropic rearrangements
Journal of Molecular Structure: THEOCHEM, 1985The semi-empirical MNDO-SCF method, extended with a limited (3 × 3) CI, has been used to calculate the photochemical (1, 3) shifts in propene, 2-propen-1-ol, 1-butene and the (1, 5) shifts in 1,3-pentadiene and 1,3-hexadiene. The suprafacial and antarafacial reactions as considered by Woodward and Hoffmann are compared with a planar shift which is ...
Guido J.M. Dormans+2 more
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The first total synthesis of the Calabar bean alkaloid geneserine (1) starting with 1-cyano-5-methoxybenzocyclobutene (7) has been accomplished via a 16-step sequence in 27% overall yield.
K. Shishido+4 more
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Electrochemical Allylic C(sp3)-H Isothiocyanation via [3,3]-Sigmatropic Rearrangement.
Organic LettersThe direct allylic C(sp3)-H functionalization provides a straightforward protocol for the synthesis of valuable molecules. We report herein the first chemo- and site-selective method for allylic C(sp3)-H isothiocyanation of various internal alkenes under
Xuezhuang Gao+6 more
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Asymmetric Iodonio-[3,3]-Sigmatropic Rearrangement to Access Chiral α-Aryl Carbonyl Compounds.
Journal of the American Chemical Society, 2020Here we describe an asymmetric [3,3]-sigmatropic rearrangement of aryl iodanes that enables the enantioselective α-arylation of chiral 2-oxazolines, thereby producing valuable, chiral α-aryl carbonyl compounds.
Junsong Tian+8 more
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Pericyclic Reactions: Cycloadditions, Electrocyclic Reactions, and Sigmatropic Rearrangements
2013This chapter covers pericyclic reactions and their its types. In these so-called pericyclic reactions, all the bond forming and bond breaking occurs together with a nonpolar, concerted cyclic redistribution of valence electrons via aromatic transition structures.
Tadashi Okuyama, Howard Maskill
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Tandem Electrocyclic‐Sigmatropic Reaction of Benzocyclobutenes.
, 1986Das Methoxybenzocyclobuten (I) wird uber die Kondensationsprodukte (II) zu den Aldehyden (III) umgesetzt, die nach Grignard die Alkohole (V) ergeben, welche mit KOH/EtOH zu den Lactonen (VI) cyclisiert werden.
K. Shishido+3 more
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Studies dealing with cycloaddition and sigmatropic reactions of cyclopropenyl-substituted indenes
The Journal of Organic Chemistry, 1991AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Diana M. Cordova+2 more
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Z-Selective α-Arylation of α,β-Unsaturated Nitriles via [3,3]-Sigmatropic Rearrangement.
Angewandte Chemie, 2020Morita-Baylis-Hillman (MBH) reaction and [3,3]-sigmatropic rearrangement are two paradigms in organic synthesis. By merging the two types of reactions, we herein describe [3,3]-rearrangement of aryl sulfoxides with α,β-unsaturated nitriles.
Mengyuan Chen+9 more
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Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines
Chinese journal of chemistryAllenes, served as highly sought‐after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties of organic compounds make allenes a desirable choice in ...
Huihui Feng+5 more
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The Reformatsky–Claisen reaction, a new synthetically useful sigmatropic process
J. Chem. Soc., Chem. Commun., 1973Reaction of α-bromo-esters derived from allylic and acetylenic alcohols with zinc dust provides a useful synthesis of γδ-unsaturated acids, via[3,3]-sigmatropic rearrangement of the intermediate zinc enolate, the efficiency depending upon substitution and solvent.
Jack E. Baldwin, Jerry A. Walker
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