Relevant bibliographies by topics / Annulation reactions

Academic literature on the topic 'Annulation reactions'

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Published: 6 September 2023

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Journal articles on the topic "Annulation reactions"

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Fang, Lei, Alexander Kalin, and Jongbok Lee. "Annulation Reactions for Conjugated Ladder-Type Oligomers." Synlett 29, no. 08 (February 27, 2018): 993–98. http://dx.doi.org/10.1055/s-0036-1591945.

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Conjugated ladder-type oligomers are a class of important functional organic materials. They possess intriguing properties stemming from their fully fused aromatic backbones. The construction of the ladder-type backbone relies on a ‘ladderization’ step, which may be accomplished through either kinetically or thermodynamically controlled annulation reactions. The attributes of these reactions are discussed, with relevant recent examples. The development of these reactions is key to continued advances and innovation in the field of organic conjugated materials.1 Introduction2 Kinetic Annulations3 Thermodynamic Annulations4 Future Outlooks and Conclusion
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Song, Ren-Jie, Bin Wei, Ke-Wei Li, Yan-Chen Wu, and Shi-Qi Tong. "Radical Strategy for the Transition-Metal-Catalyzed Synthesis of γ-Lactones: A Review." Synthesis 52, no. 24 (June 8, 2020): 3855–65. http://dx.doi.org/10.1055/s-0040-1707835.

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The γ-lactone skeleton is very important component of various natural products, biological molecules, food additives, and perfumes. As a result, much effort has been made towards such compounds. In this review, we summarize recent progress in transition-metal-catalyzed annulation reactions for the formation of γ-lactone derivatives through a radical pathway. Various reagents, such as anhydrides, Togni’s reagent, TMSN3, arenesulfonyl chlorides, arenediazonium salts, dibenzoyl peroxides, O-benzoylhydroxylamine, NFSI, and α-halocarboxylic compounds, used in radical cyclization reactions are described, and the mechanisms of these radical annulation reactions are also discussed.1 Introduction2 Annulations of Alkenes with Anhydrides3 Annulations of Unsaturated Carboxylic Acids with Nucleophiles4 Annulations of Alkenes with α-Halocarboxylic Compounds5 Conclusions and Outlook
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Comesse, Sébastien, Ismail Alahyen, Laure Benhamou, Vincent Dalla, and Catherine Taillier. "20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions." Synthesis 53, no. 19 (May 10, 2021): 3409–39. http://dx.doi.org/10.1055/a-1503-7932.

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AbstractAcrylamides are versatile building blocks that are easily obtained from readily available starting materials. During the last 20 years, these valuable substrates bearing a nucleophilic nitrogen atom and an electrophilic double bond have proven to be efficient domino partners, leading to a wide variety of complex aza-heterocycles of synthetic relevance. In this non-exhaustive review, metal-free and metal-triggered reactions followed by an annulation will be presented; these two approaches allow good modulation of the reactivity of the polyvalent acrylamides.1 Introduction2 Metal-Free Annulations2.1 Domino Reactions Triggered by a Michael Addition2.2 Domino Reactions Triggered by an Aza-Michael Addition2.3 Domino Processes Triggered by an Acylation Reaction2.4 Domino Reactions Triggered by a Baylis–Hillman Reaction2.5 Cycloadditions and Domino Reactions2.6 Miscellaneous Domino Reactions3 Metal-Triggered/Mediated Annulations3.1 Zinc-Promoted Transformations3.2 Rhodium-Catalyzed Functionalization/Annulation Cascades3.3 Cobalt-Catalyzed Functionalization/Annulation Cascades3.4 Ruthenium-Catalyzed Functionalization/Annulation Cascades3.5 Iron-Catalyzed Functionalization/Annulation Cascades3.6 Palladium-Catalyzed Functionalization/Annulation Cascades3.7 Copper-Catalyzed Transformations3.8 Transition Metals Acting in Tandem in Domino Processes4 Radical Cascade Reactions5 Conclusion
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Gerasyuto, Aleksey I., Zhi-Xiong Ma, Grant S. Buchanan, and Richard P. Hsung. "Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis." Beilstein Journal of Organic Chemistry 9 (June 18, 2013): 1170–78. http://dx.doi.org/10.3762/bjoc.9.131.

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A successful enone version of an intramolecular aza-[3 + 3] annulation reaction is described here. Use of piperidinium trifluoroacetate salt as the catalyst and toluene as the solvent appears to be critical for a successful annulation. We also demonstrated for the first time that microwave irradiation can accelerate aza-[3 + 3] annulation reactions. An attempt to expand the scope of the enone aza-[3 + 3] annulation was made in the form of propyleine synthesis as a proof of concept. While synthesis of the enone annulation precursor was successfully accomplished, the annulation proved to be challenging and was only modestly successful.
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Cardoso, Ana L., and Maria I. L. Soares. "1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings." Current Organic Chemistry 23, no. 27 (January 15, 2020): 3064–134. http://dx.doi.org/10.2174/1385272823666191203122959.

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The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked. This review summarizes the most relevant research in which allenes are used as building blocks for the construction of structurally diverse five-membered rings via [3+2] annulation reactions.
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Mao, Guoliang, Qiang Huang, and Congyang Wang. "Rhenium-Catalyzed Annulation Reactions." European Journal of Organic Chemistry 2017, no. 25 (May 23, 2017): 3549–64. http://dx.doi.org/10.1002/ejoc.201700285.

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Jeganmohan, Masilamani, and Pinki Sihag. "Recent Advances in Transition-Metal-Catalyzed C–H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes." Synthesis 53, no. 18 (June 14, 2021): 3249–62. http://dx.doi.org/10.1055/a-1528-1711.

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AbstractBicyclic alkenes, including oxa- and azabicyclic alkenes, readily undergo activation with facial selectivity in the presence of transition-metal complexes. This is due to the intrinsic angle strain on the carbon–carbon double bonds in such unsymmetrical bicyclic systems. During the past decades considerable progress has been made in the area of ring opening of bicyclic strained rings by employing the concept of C–H activation. This short review comprehensively compiles the various C–H bond activation assisted reactions of oxa- and azabicyclic alkenes, viz., ring-opening reactions, hydroarylation, and annulation reactions.1 Introduction2 Reactions of Heterobicyclic Ring Systems2.1 Ring-Opening Reactions of Oxa- and Azabenzonorbornadienes2.1.1 Reactions Using 7-Oxabenzonorbornadienes2.1.2 Reactions Using 7-Azabenzonorbornadienes2.2 Hydroarylation Reactions2.3 Annulation Reactions2.4 Other Reactions3 Conclusion
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Li, Yangyan, Xiang Chen, Xiaoming Chen, and Xiao Shen. "Organophosphine-Catalyzed [4C+X] Annulations." Molecules 23, no. 11 (November 19, 2018): 3022. http://dx.doi.org/10.3390/molecules23113022.

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In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5–8-membered cyclic products. In this short overview, we summarize the remarkable progress, emphasizing reaction mechanisms and key intermediates involved in the processes. The discussion is classified according to the type of electrophilic reactants that acted as C4 synthons in the annulation process, in the order of α-alkyl allenoates, γ-alkyl allenoates, α-methyl allene ketones, β′-OAc allenoate, δ-OAc allenoate, activated dienes and cyclobutenones.
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Dillon, John L., Qi Gao, Elizabeth A. Dillon, and Nick Adams. "New annulation reactions of cyclobutenones." Tetrahedron Letters 38, no. 13 (March 1997): 2231–34. http://dx.doi.org/10.1016/s0040-4039(97)00331-6.

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Qian, Hui, Wanxiang Zhao, and Jianwei Sun. "Siloxy Alkynes in Annulation Reactions." Chemical Record 14, no. 6 (August 29, 2014): 1070–85. http://dx.doi.org/10.1002/tcr.201402042.

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Dissertations / Theses on the topic "Annulation reactions"

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Baxter, John S. "Transition metal mediated annulation reactions." Thesis, University of Bristol, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.324243.

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Heshmati, Parissa. "Novel annulation reactions using cobalt stabilised carbonium ions." Thesis, Kingston University, 1994. http://eprints.kingston.ac.uk/20573/.

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This programme of work was aimed at the synthesis of a range of linear hydrocarbon molecules bearing functionality at each end. It was envisaged that by the application of an intramolecular Nicholas reaction the linear chain would cyclise to afford an [alpha],[beta] disubstituted cycloalkanone. The Nicholas reaction is based on the propargyl carbonium ions, stabilised with binuclear cobalt species, which are subject to nucleophilic attack at the propargyl position. This reaction has previously been exploited in syntheses in an intermolecular fashion, however, few approaches involving an intramolecular reaction have appeared in the literature. Thus, in the present study, investigation of the latter was undertaken. In this novel approach a series of 5,6 or 7 membered carbocyclic compounds were synthesised from precursor molecules containing 8,9,10 or 11 carbon chains. During this exercise one or two asymmetric centres were also created in a series of reactions that are the equivalent of a 1,4-addition of ethyne to an enone. All the synthetic steps were thoroughly investigated and optimised. It was also demonstrated that for unsymmetrical linear ketones, the kinetic enolates seem to predominate irrespective of the reaction conditions employed. This was in contrast to enolate formation in unsymmetrically substituted cyclic ketones, where selectivity between the kinetic and thermodynamic enolates has been observed by appropriate choice of base. Infra-red, [sup]1H N.M.R., [sup]13C N.M.R. and Mass spectroscopy analyses were performed on all the compounds synthesised. However cobalt complexed compounds showed some paramagnetism, possibly due to the presence of some paramagnetic impurities or by-products. This led to difficulties in interpretation of spectra as a result of line broadening. Future work might usefully investigate the use of these methodologies in the synthesis of fused carbocycles, heterocycles and highly functionalised fused ring systems, generated from a tandem intramolecular reaction involving a Nicholas reaction followed bya Pauson-Khand reaction.
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Sabin, Verity Margaret. "Synthetic studies on two silicon assisted annulation reactions." Thesis, University of Cambridge, 1994. https://www.repository.cam.ac.uk/handle/1810/272796.

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Liu, Yang. "Studies on Palladium-Catalyzed [3+2]-Annulation/Domino Reactions." Thesis, Sorbonne université, 2019. http://www.theses.fr/2019SORUS214.

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Ce travail de thèse est consacré à l'étude des réactions d'annélation [3+2] domino catalysées au palladium. Tout d'abord, une nouvelle séquence domino a été développée, qui implique la réaction entre les dérivés cycliques α,β-insaturés-γ-oxy-carbonylés et les acétamides stabilisés par résonance. Les pyrrolidine-2-ones bicycliques obtenues ont été générées par une allylation intermoléculaire catalysée au Pd, suivie d'une réaction d’aza-Michael intramoléculaire. Une version asymétrique a également été réalisée, obtenant jusqu'à 60% d’excès énantiomérique. Ensuite, une nouvelle séquence domino triple catalysée au Pd [allylation / aza-Michael / keto α-arylation] (ALAMAR) a également été réalisée, ce qui permet la formation sélective de systèmes tricycliques fusionnés en un seul pot. Enfin, deux transformations domino sélectives et complémentaires ont été réalisées, permettant d'effectuer au choix des annulations de type C−C/O−C ou C−C/C−C [3+2]. Ces transformations se produisent par le biais d'une séquence de [C-allylation intermoléculaire / O- ou C-1,4-addition conjuguée intramoléculaire]
This thesis work is consecrated to the study of palladium-catalyzed [3+2]-annulation and domino reactions. First, a new domino sequence was developed, which involves the reaction between cyclic α,β-unsaturated-γ-oxy-carbonyl derivatives and resonance-stabilized acetamides. The resulting bicyclic pyrrolidin-2-ones were generated through an intermolecular Pd-catalyzed allylation followed by an intramolecular aza-Michael reaction sequence. An asymmetric version was also achieved, obtaining up to 60% ee. A new Pd-catalyzed [allylation / aza-Michael / keto α-arylation] (ALAMAR) triple domino sequence was also accomplished, which allows the selective one-pot formation of fused tricyclic systems. Lastly, two selective and complementary domino transformations have been achieved, which allow to perform C−C/O−C or C−C/C−C [3+2]-annulations at will. These transformations occur through an intermolecular Pd-catalyzed C-allylation / intramolecular O- or C-1,4-addition sequence, respectively
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Flanagan, Stuart Robert. "New aromatic annulation reactions and their application in total synthesis." Thesis, University of Southampton, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.402059.

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Chogii, Isaac, and Isaac Chogii. "New Anionic Annulation Reactions and Anion Accelerated Amino-Cope Rearrangement." Diss., The University of Arizona, 2016. http://hdl.handle.net/10150/621558.

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New Anionic Annulation Reactions and Anion Accelerated Amino-Cope Rearrangement. This dissertation compiles asymmetric anionic reactions of chiral Ellman sulfinyl imines and dienolates to access diverse nitrogen-containing compounds. Chiral sulfinimines and dienolates derived from 𝛾-bromocrotonates reacted diastereoselectively forming 3-pyrrolines and 𝑐𝑖𝑠-vinyl aziridines via a formal [3+2]-annulation and vinylogous 𝑎𝑧𝑎-Darzens reactions respectively. Concise asymmetric syntheses of three natural products have been achieved demonstrating the power of the [3+2]-methodology. Reaction of conjugated sulfinimines with enolates derived from non-halogen containing crotonates, were found to undergo a tandem diastereoselective α,α-addition, and anionic [3,3]-rearrangement affording vinylogous amide products. Synthesis of aromatic imines via 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) initiated oxidative aromatization highlights the synthetic value of the accelerated anion amino-Cope rearrangement.
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Emrullahoglu, Mustafa. "Novel Annulation Reactions For The Synthesis Of Substituted Pyrroles Darzens Reaction Of Acyl Phosphonates With &amp." Phd thesis, METU, 2009. http://etd.lib.metu.edu.tr/upload/3/12610338/index.pdf.

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In the first part of this thesis, it is aimed to develope methods for the synthesis of trisubstituted pyrrrole derivatives. 2-Aminopyrrroles, alkoxy and sulfonyl substittitued pyrrole derivatives as well as pirolinones show interesting biological activities and are precursor of well know drugs. Although there is a number of methods for the synthesis of pyrroles, the synthesis of 2-aminopyrroles is limited to few works and is not widely known. Therefore, it is still an important goal in organic chemistry to improve methods for the synthesis of multifunctionalized pyrrole derivatives and pyrrolinones. Alkylation of &
#946
-dicarbonyl compounds with bromoacetonitrile furnishes &
#945
- cyanomethyl-&
#946
-dicarbonyl compounds. The condensation reaction of &
#945
- v cyanomethyl-&
#946
-dicarbonyl compounds with amines catalyzed by p-TsOH affords the corresponding enamines and further base catalyzed cyclization furnishes 2- aminopyrroles in high yields, moreover, zinc perchlorate-catalyzed addition of amines, alcohols and thiols to the nitrile carbon of &
#945
-cyanomethyl-&
#946
-ketoesters followed by annulation gives the 5-alkoxy and 5-alkylsulfanylpyrrole-3-carboxylates in high yields. In the second part of the thesis, reactions of a broad range of acyl phosphonates with &
#945
-bromo acetophenones at room temperature in the presence of different bases were described to afford two diastereomeric epoxy phosphonates in good yields and high diastereoselectivities. The diastereoselectivity of this reaction is easily controlled by changing the base. Accordingly, changing the base from Cs2CO3 to DBU changes the diatereomeric ratio (trans/cis) from 5/3 to 9/1. Furthermore, the treatment of trans isomer with DBU shows a complete conversion to the corresponding cis isomer. Additionally, these highly functionalized epoxyphosphonates are shown to be useful intermediates to give several reactions
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Marais, Pierre Christiaan. "New annulation methods : total synthesis of the diterpenoid (+--)-ambliol B." Thesis, University of British Columbia, 1990. http://hdl.handle.net/2429/30639.

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The preparation of bicyclic systems containing an allylic, angular hydroxyl group (general structure 20 and compound 87b) is described. These materials have been prepared via a new annulation sequence involving (a) the alkylation of cyclic ketones with the bifunctional conjunctive reagents 129, 21 and 60, (b) the conversion of the alkylation products into keto vinyl iodides, and (c) cyclization of the keto vinyl iodides via low temperature metal halogen exchange with n-butyllithium. The cyclization process described in (c) has been employed in the first total synthesis of the diterpenoid (±)-ambliol B (94). Thus, 3,4-dimethyl-2-cyclohexen-l-one (96) was converted, in three steps, into the unstable enone 125. Reaction of this compound with the novel vinylgermane cuprate 110, followed by reaction of the resultant product with iodine, gave the cyclization precursor 106. Cyclization of 106 gave a single, trans-fused product (128) in high yield. The exocyclic methylene function of 128 was cyclopropanated and the vinyl substituent of the resultant cyclopropane was hydroborated to give the cyclopropane diol 149. Hydrogenolysis of the cyclopropane ring of compound 149 provided the required gem-dimethyl moiety. The resultant product was converted into (±)-ambliol B (94) via a four step sequence of reactions involving (a) oxidation of the primary alcohol function, (b) addition of 3-furyllithium to the so-formed unstable aldehyde, (c) acetylation of the secondary alcohol prepared in (b), and (d) reductive removal of the acetoxy function. A new annulation sequence which utilizes the vinylgermane cuprate 110 as a synthetic equivalent of the 1-butene a²,d⁴-synthon 153 is described. Thus, cyclic enones of the general structure 154 were treated with 110 to provide the keto vinylgermane intermediates 155. The latter materials were transformed into the corresponding keto vinyl iodides 156. Treatment of 156 with a palladium(0) catalyst and a base resulted in cyclization to provide the annulation products 157 or, when R₁ = H, the α,β-unsaturated ketones 185. [ Formulas omitted ]
Science, Faculty of
Chemistry, Department of
Graduate
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9

Davie, Christopher P. "[4 + 1] annulation reactions of (trialkylsilyl)ketenes : synthesis of substituted indanones and cyclopentenones." Thesis, Massachusetts Institute of Technology, 2005. http://hdl.handle.net/1721.1/33648.

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Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2005.
Vita.
Includes bibliographical references.
(Trialkylsilyl)vinylketenes ("(TAS)vinylketenes") and (trialkylsilyl)arylketenes ("(TAS)- arylketenes") function as versatile four-carbon building blocks for the synthesis of carbocyclic and heterocyclic compounds. A new [4 + 1] annulation strategy for the synthesis of substituted 2-indanones, based on the reaction of TAS-arylketenes with trimethylsilyl diazomethane, has been developed. In addition, a new class of carbenoid reagents for our previously reported [4 + 1] cyclopentenone annulation has been identified. Studies have shown that the reaction of a- benzotriazolyl organolithium compounds (prepared via metallation of readily available N- substituted benzotriazole derivatives) with (TAS)vinylketenes generates dienolate intermediates which cyclize to form cyclopentenones. Most cases of the annulation proceed with a high level of diastereoselectivity, and deliver highly substituted and functionalized 2-silylcyclopentenones in good yield. Furthermore, the vinylsilane moiety incorporated in the [4 + 1] annulation products provides a useful handle for further synthetic transformations. Preliminary studies focused on elaboration of the cyclopentenone products have laid the groundwork for future applications of this [4 + 1] annulation methodology.
by Christopher P. Davie.
Ph.D.
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Ashida, Shinji. "Development of Nickel-Catalyzed Annulation Reactions Using Cyclobutanones as a Four-Carbon Unit." 京都大学 (Kyoto University), 2008. http://hdl.handle.net/2433/61312.

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Kyoto University (京都大学)
0048
新制・課程博士
博士(工学)
甲第14053号
工博第2965号
新制||工||1440(附属図書館)
26332
UT51-2008-F445
京都大学大学院工学研究科合成・生物化学専攻
(主査)教授 村上 正浩, 教授 吉田 潤一, 教授 杉野目 道紀
学位規則第4条第1項該当
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Books on the topic "Annulation reactions"

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Novikov, Roman, Denis Borisov, Leonid Menchikov, and Yuriy Tomilov. Donor-acceptor cyclopropanes. Cycloaddition and annulation reactions. LCC MAKS Press, 2022. http://dx.doi.org/10.29003/m2659.978-5-317-06797-7.

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This is the second book in the Donor-Acceptor Cyclopropanes series. It summarizes and analyzes for the first time the main intermediates formed from D-A cyclopropanes, and also systematizes the main ways of their further transformations. The main attention is paid to the cycloaddition and annulation reactions of D-A cyclopropanes with various substrates under the action of Lewis acids, which are of the greatest practical importance in organic synthesis. The monograph is addressed to a wide range of specialists in the field of small cycle chemistry and organic synthesis, including the synthesis of natural compounds and biologically active substances
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Faron, Katherine L. Reactions of Fischer carbene complexes with unsaturated organic substrates: Studies of the Ene, [2+2] and alkyne annulation processes. 1989.

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Mal, Dipakranjan. Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-Forming Reactions. Elsevier, 2018.

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Mal, Dipakranjan. Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-Forming Reactions. Elsevier, 2018.

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Book chapters on the topic "Annulation reactions"

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Li, Jie Jack. "Robinson annulation." In Name Reactions, 340. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_253.

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Li, Jie Jack. "Danheiser annulation." In Name Reactions, 102. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_80.

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Li, Jie Jack. "Robinson annulation." In Name Reactions, 519–20. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_234.

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Li, Jie Jack. "Danheiser annulation." In Name Reactions, 194–95. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_81.

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Li, Jie Jack. "Robinson annulation." In Name Reactions, 309. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_242.

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Li, Jie Jack. "Danheiser annulation." In Name Reactions, 90. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_75.

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Li, Jie Jack. "Robinson annulation." In Name Reactions, 470–71. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_219.

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Li, Jie Jack. "Robinson Annulation." In Name Reactions, 474–76. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_131.

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Dötz, Karl Heinz. "Carbene Complexes in Selective Organic Synthesis: Novel Applications of Carbene Annulation Reactions." In Advances in Metal Carbene Chemistry, 199–210. Dordrecht: Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-2317-1_25.

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Werz, Daniel B. "Adding Additional Rings to the Carbohydrate Core: Access via (SPIRO) Annulation Domino Processes." In Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience, 195–208. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2016. http://dx.doi.org/10.1002/9781119044222.ch8.

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