Relevant bibliographies by topics / Sigmatropic rearrangements

Contents

  1. Journal articles

Academic literature on the topic 'Sigmatropic rearrangements'

Author: Grafiati
Published: 4 June 2021
Last updated: 11 June 2025

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the lists of relevant articles, books, theses, conference reports, and other scholarly sources on the topic 'Sigmatropic rearrangements.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Journal articles on the topic "Sigmatropic rearrangements"

1

Zhang, Lei, Mengjie Hu, and Bo Peng. "[3,3]- and [5,5]-Sigmatropic Rearrangements of Aryl Sulfoxides Using An ‘Assembly/Deprotonation’ Technology." Synlett 30, no. 20 (2019): 2203–8. http://dx.doi.org/10.1055/s-0039-1690212.

Full text
Abstract:
The redox-neutral ortho-functionalizations of aryl/heteroaryl sulfoxides via interrupted Pummerer processes have been greatly advanced since its discovery by Kita and Padwa in the early 2000s. In this context, we recently developed an ortho-cyanoalkylation of aryl sulfoxides with alkyl nitriles using an ‘assembly/deprotonation’ protocol. The success of the reaction hinges on the independent control of the electrophilic assembly of both coupling partners and subsequent deprotonation of the in situ generated imine sulfonium intermediates. Further [3,3]-sigmatropic rearrangement of the in situ formed ketenimine sulfonium species furnishes ortho-cyanoalkylated aryl sulfides. More recently, we also applied the ‘assembly/deprotonation’ strategy for the development of the [5,5]-sigmatropic rearrangement of aryl sulfoxides with allyl nitriles that allows for para-cyanoalkylation of aryl sulfoxides. The development of these two reactions is described in this Synpacts article.1 Background2 [3,3]-Sigmatropic Rearrangement3 [5,5]-Sigmatropic Rearrangement4 Conclusion
APA, Harvard, Vancouver, ISO, and other styles
2

Zhang, Beibei, Xiaoxian Li, Boying Guo, and Yunfei Du. "Hypervalent iodine reagent-mediated reactions involving rearrangement processes." Chemical Communications 56, no. 91 (2020): 14119–36. http://dx.doi.org/10.1039/d0cc05354f.

Full text
Abstract:
We summarize the developments of hypervalent iodine reagents-mediated reactions involving [1,2]-migration, Hofmann rearrangement, Beckmann rearrangement, ring contraction/expansion, [3,3]-sigmatropic/iodonium-Claisen rearrangement and some miscellaneous rearrangements.
APA, Harvard, Vancouver, ISO, and other styles
3

Nohira, Hiroyuki, and Toshiyuki Nohira. "Dynamic correlation diagrams for sigmatropic reactions based on orbital phase conservation theory." Journal of Theoretical and Computational Chemistry 16, no. 06 (2017): 1750055. http://dx.doi.org/10.1142/s0219633617500559.

Full text
Abstract:
For sigmatropic reactions, such as [1,3] and [1,5] hydrogen shifts, the Cope and Claisen rearrangements, and the Berson–Nelson rearrangement, no correlation diagrams consistent with the classical electronic formulas have been reported. Here, we report dynamic correlation diagrams for these sigmatropic reactions based on orbital phase conservation theory. The diagrams are consistent with both the selection rules of sigmatropic reactions proposed by Woodward and Hoffmann and classical electronic formulas.
APA, Harvard, Vancouver, ISO, and other styles
4

Ficeri, Vlastimír, Peter Kutschy, Milan Dzurilla, and Ján Imrich. "[3,3]- Versus [1,3]-Sigmatropic Rearrangement of O-Substituted Allyl N-Acylmonothiocarbamates." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2650–62. http://dx.doi.org/10.1135/cccc19942650.

Full text
Abstract:
Substituted allylic alcohols (2-buten-1-ol, 1-buten-3-ol, cinnamyl alcohol and 3-methyl-2-buten-1-ol) react with acyl isothiocyanates (4-chlorobenzoyl, 2,6-difluorobenzoyl, 3-phenylpropenoyl, 2-thienocarbonyl, 3-chloro-2-thienocarbonyl and 3-chloro-2-benzo[b]thienocarbonyl isothiocyanate) with the formation of highly reactive O-substituted allyl N-acylmonothiocarbamates, which either spontaneously or by heating in boiling benzene undergo [3,3]-sigmatropic rearrangement to S-substituted allyl N-acylmonothiocarbamates. The structure of S-esters with isomerized allylic group affords the unequivocal evidence of the [3,3]-sigmatropic route of studied rearrangement. Further heating of [3,3]-rearranged N-(4-chlorobenzoyl)monothiocarbamates results in the [1,3]-sigmatropic shift of monothiocarbamate group. Using arylalkyl alcohols with the allylic double bond inserted into an aromatic system the obtained O-esters either do not undergo any rearrangement (benzyl alcohol) or undergo [1,3]-sigmatropic rearrangement (2- and 3-furylmethanol and 1-(2-furyl)ethanol) to the corresponding S-esters. For explanation of this reaction the tandem of [3,3]- and [1,3]-sigmatropic rearrangements is suggested.
APA, Harvard, Vancouver, ISO, and other styles
5

Dudziński, Piotr, Wibke S. Husstedt, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5607–23. http://dx.doi.org/10.1039/d1ob00870f.

Full text
Abstract:
[3,3]-Sigmatropic rearrangements based on different SF<sub>5</sub>-substituted allylic alcohols were investigated. The synthetic sequence developed for SF<sub>5</sub> compounds is also useful for CF<sub>3</sub> analogues and its application in Johnson–Claisen rearrangement.
APA, Harvard, Vancouver, ISO, and other styles
6

Zeh, J., and M. Hiersemann. "ChemInform Abstract: Sigmatropic Rearrangements." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142241.

Full text
APA, Harvard, Vancouver, ISO, and other styles
7

Villalva-Servín, Nidia P., Alain Laurent, and Alex G. Fallis. "Part 2: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB-taxane ring systems) and their conversion to tricyclo[9.3.1.03,8]pentadecenones (ABC taxane ring systems) and bicyclo[2.2.2]octanones." Canadian Journal of Chemistry 82, no. 2 (2004): 227–39. http://dx.doi.org/10.1139/v03-201.

Full text
Abstract:
The extension of our strategies for the construction of cyclic molecules containing variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems) for the synthesis of the tricyclo[9.3.1.03,8]pentadecenone (ABC taxane ring system) and bicyclo[2.2.2]octanones are described. These routes employ a multi-component coupling protocol that employs sequential magnesium-mediated carbometallation of allyl-substituted propargyl alcohols followed by diastereoselective Lewis acid catalyzed intramolecular Diels–Alder reactions (IMDA). Subsequent ring-closing metathesis (RCM) afforded the ABC taxane core structure. Enone accelerated [3,3] sigmatropic rearrangements (Cope rearrangements) generated the bicyclo[2.2.2]octanone nucleus. In the presence of a Lewis acid, the dienophile precursor underwent a tandem reaction via the adduct directly to the bicyclo[2.2.2]octanones. This is the first example of a novel enone accelerated carbocycle Cope rearrangement and provides direct access to bicyclo[2.2.2]octanones by a new route that compliments the traditional cyclohexadiene cycloaddition approach. Key words: magnesium chelate, Lewis acid, taxanes, Diels–Alder, sigmatropic rearrangement, oxy-Cope, ring-closing metathesis, bicyclo[2.2.2]octanone.
APA, Harvard, Vancouver, ISO, and other styles
8

Belaissaoui, Abdelhak, Sandrine Jacquot, Claude Morpain, Gérard Schmitt, Joël Vebrel, and Bernard Laude. "Réactivité dipolaire-1,3 du 4,4,4-trichiloro-3-éthoxycarbonylamino-2-diazobutyrate d'éthyle issu de l'action du diazoacétate d'éthyle sur la N-éthoxycarbonyl-N-(2,2,2-trichloroéthylidène)amine." Canadian Journal of Chemistry 75, no. 5 (1997): 523–30. http://dx.doi.org/10.1139/v97-061.

Full text
Abstract:
The reaction of ethyl diazoacetate with the N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine yields, by a nucleophilic addition, a new diazo compound that gives 1,3-dipolar cycloaddition reactions with acetylenic esters and maleimides. With acetylenic esters, the cycloadduct leads to substituted pyrazoles by [1,5] sigmatropic rearrangements. With maleimides, we observe a diastereospecific cycloaddition reaction. The intermediary cycloadduct evolves by nitrogen elimination to give a maleimidocyclopropane. The diastereospecificity was explained by an endo-anti approach of the reactants. Keywords: N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine, ethyl diazoacetate, nucleophilic addition, 1,3-dipolar cycloaddition, sigmatropic rearrangement, diastereoselectivity.
APA, Harvard, Vancouver, ISO, and other styles
9

Ernouf, Guillaume, Jean-Louis Brayer, Christophe Meyer, and Janine Cossy. "Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes." Beilstein Journal of Organic Chemistry 15 (February 5, 2019): 333–50. http://dx.doi.org/10.3762/bjoc.15.29.

Full text
Abstract:
Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished through different strategies, this review is focusing specifically on the use of [2,3]- and [3,3]-sigmatropic rearrangements involving cyclopropenylcarbinol derivatives as substrates. These sigmatropic rearrangements, which have been developed in recent years, allow a remarkably efficient and stereoselective access to a wide variety of heterosubstituted and/or functionalized alkylidenecyclopropanes which would not be readily accessible by other strategies. The different [2,3]- and [3,3]-sigmatropic rearrangements of cyclopropenylcarbinol derivatives disclosed to date, as well as the analysis of their substrate scope and some applications of the products arising from those reactions, are presented in this review.
APA, Harvard, Vancouver, ISO, and other styles
10

Frampton, Christopher S., Michael W. Majchrzak, and John Warkentin. "Sense of sequential 1,5-sigmatropic rearrangements of dimethyl-3,3-dialkyl-3H-pyrazole-4,5-dicarboxylates. Crystal and molecular structures of two dimethyl-4,5-dialkyl-1H-pyrazole-1,3-dicarboxylates." Canadian Journal of Chemistry 69, no. 3 (1991): 373–78. http://dx.doi.org/10.1139/v91-057.

Full text
Abstract:
3,3-Dialkyl-3H-pyrazole-4,5-dicarboxylic acid dimethyl esters (4), obtained by cycloaddition of R1R2C=N+=N− (R1 = R2 = CH3; R1 = CH3, R2 = CH2CH3) to CH3O2CC≡CCO2CH3, rearrange thermally by 1,5-sigmatropic alkyl shifts to both N and C. The latter rearrangement is followed by two successive 1,5-sigmatropic shifts of a methoxycarbonyl group. Final products of the threefold rearrangement were shown to be 4,5-dialkyl-1H-pyrazole-1,3-dicarboxylic acid dimethyl esters (6), rather than the isomeric 3,4-dialkyl-1H-pyrazole-1,5-dicarboxylic acid dimethyl esters (7), by means of single crystal X-ray diffraction. Those products therefore result from alkyl migration to C-4 of 4, followed by sequential migration of the methoxycarbonyl group, initially at C-4, to C-3 and then to N-2 of 4. In the initial alkyl migration step, ethyl migrates in preference to methyl, and in subsequent migration steps the methoxycarbonyl group migrates faster than the ethyl or methyl group. Crystals of 4-ethyl-5-methyl-1H-pyrazole-1,3-dicarboxylic acid dimethyl ester (6b) are monoclinic, of space group P21/n, with a = 7.907(1) Å, b = 11.087(2) Å, c = 13.199(3) Å, V = 1124.9(4) Å 3, Dc = 1.34 g cm−3, Dm = 1.33 g cm−3 for Z = 4, and R1 = 0.0772 (R2 = 0.0626) for 1474 reflections (R1 = 0.0428, R2 = 0.0422 for 903 reflections with I &gt; 3σ(I)). The structure of 6a is similar. Key words: 3,3-dialkyl-3H-pyrazoles, 1,5-sigmatropic rearrangements of; 4,5-dialkyl-1H-pyrazoles, crystal and molecular structures; 1,5-sigmatropic rearrangements of pyrazoles, sense of.
APA, Harvard, Vancouver, ISO, and other styles
More sources
You might also be interested in the extended bibliographies on the topic 'Sigmatropic rearrangements' for particular source types:
Journal articles
We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!

To the bibliography