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1

Mulzer, Johann, Dirk Trauner та Jan W. Bats. "Stereoselective Insertion of Ketenes into O,O-Acetals: Synthesis ofβ-Alkoxy Esters and 1,4-Dioxepan-5-ones". Angewandte Chemie International Edition in English 35, № 17 (1996): 1970–72. http://dx.doi.org/10.1002/anie.199619701.

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2

Charlton, M. Anne, and James R. Green. "Formation of quaternary centres via iron allyl cations. Rapid entry into spirocyclic ring systems." Canadian Journal of Chemistry 75, no. 7 (1997): 965–74. http://dx.doi.org/10.1139/v97-116.

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Ester-substituted allyltetracarbonyliron cations react with cycloalkylidene-type silyl enol ethers, silyl ketene acetals, and β-keto-esters to give 1,6-dicarbonyl compounds containing a newly formed quaternary centre. Selected condensation products are converted by enolate chemistry into spirocyclic [4.4], [4.5], and [4.6] systems. Acyloin and other reductive cyclization reactions are employed to convert the condensation products into spirocyclic [4.5], [5.5], and [5.6] systems. Keywords: allyliron complexes, umpolung synthesis, 1,6-dicarbonyls, spirocycle synthesis.
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3

Lampland, Nicole L., Aradhana Pindwal, Steven R. Neal, Shealyn Schlauderaff, Arkady Ellern та Aaron D. Sadow. "Magnesium-catalyzed hydrosilylation of α,β-unsaturated esters". Chemical Science 6, № 12 (2015): 6901–7. http://dx.doi.org/10.1039/c5sc02435h.

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4

Jackson, Alexander W., Srinivasa Reddy Mothe, Lohitha Rao Chennamaneni, Alexander van Herk, and Praveen Thoniyot. "Unraveling the History and Revisiting the Synthesis of Degradable Polystyrene Analogues via Radical Ring-Opening Copolymerization with Cyclic Ketene Acetals." Materials 13, no. 10 (2020): 2325. http://dx.doi.org/10.3390/ma13102325.

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Degradable analogues of polystyrene are synthesized via radical ring-opening (co)polymerization (rROP) between styrene and two cyclic ketene acetals, namely 2-methylene-1,3-dioxepane (MDO) and 5,6-benzo-2-methylene-1,3-dioxepane (BMDO). This approach periodically inserts ester bonds throughout the main chain of polystyrene, imparting a degradation pathway via ester hydrolysis. We discuss the historical record of this approach, with careful attention paid to the conflicting findings previously reported. We have found a common 1H NMR characterization error, repeated throughout the existing body
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5

Collins, David J., and Ian T. Crosby. "Enolic Ortho Esters. VIII Synthesis of (2S,3S)-2,3-Bis(methoxymethyl)-1,4,6-trioxaspiro[4.5]dec-7-ene." Australian Journal of Chemistry 51, no. 11 (1998): 1025. http://dx.doi.org/10.1071/c98085.

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Enolic ortho ester (2S,3S)-2,3-bis(methoxymethyl)-1,4,6-trioxaspiro[4.5]dec-7-ene (10b) was synthesized in 65% yield by cycloadditon of acrolein with the ketene acetal (4S,5S)-4,5-bis(methoxymethyl)-2-methylidene-1,3-dioxolan (7), derived by potassium t-butoxide treatment of (4S,5S)-4,5-bis(methoxy- methyl)-1,3-dioxolan (4). Lewis acid catalysed reaction (TiCl4, CH2Cl2, –78°) of the enolic ortho ester (10b) with the ketene silyl acetal 3-phenylmethyl-2-trimethylsilyloxy-4,5-dihydrofuran (15) afforded the formyl keto ester 3-[4′,5′-bis(methoxymethyl)-2′-(4′′-oxobutyl)-1′,3′-dioxolan-2′-yl]-3-ph
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6

Engesser, Tobias, and Reinhard Brückner. "Stereoselective Aldol Additions of Glycolic Acid and Its Derivatives." Synthesis 51, no. 08 (2019): 1715–45. http://dx.doi.org/10.1055/s-0037-1611721.

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This review gives a comprehensive overview of aldol additions of glycolic acid derivatives to achiral aldehydes and acetals affording α,β-dihydroxycarboxylic acids or derivatives thereof. The focus is on simple diastereoselectivity. A selection of related aldol additions is also presented: aldol additions of glycolic acid derivatives to ketones with two different substituents and aldol additions of α-substituted glycolic acid derivatives.1 Introduction1.1 Organization of this Review1.2 Outside the Scope of this Review: Aldol Additions Giving α,β-Dihydroxyaldehydes and α,β-Dihydroxyketones Dias
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7

Suginome, Michinori. "Aminoboranes as new iminium ion generators in amination reactions." Pure and Applied Chemistry 78, no. 7 (2006): 1377–87. http://dx.doi.org/10.1351/pac200678071377.

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The utilization of aminoborane derivatives in amination reactions such as Strecker-type aminative cyanation, Mannich-type reaction, and reductive amination is described. Bis(dialkylamino)cyanoboranes and bis(dialkylamino)boron enolates underwent the concurrent transfer of the amino group and either the cyano or the enoxy group from the boron to carbonyl carbon atom in their reaction with aldehydes, leading to the formation of α-amino nitriles and β-amino ketones, respectively. Bis(dialkylamino)borane derivatives that lack the additional nucleophilic groups on the boron atoms were found to serv
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8

Jiang, Xingyu, and John F. Hartwig. "Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates." Angewandte Chemie International Edition 56, no. 30 (2017): 8887–91. http://dx.doi.org/10.1002/anie.201704354.

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9

Jiang, Xingyu, and John F. Hartwig. "Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates." Angewandte Chemie 129, no. 30 (2017): 9013–17. http://dx.doi.org/10.1002/ange.201704354.

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10

Collins, DJ, GLP Choo та H. Obrist. "Preparation of β-Keto Ester Acetals by Reaction of Ortho Esters With Ketene Silyl Acetals in the Presence of Titanium Tetrachloride". Australian Journal of Chemistry 43, № 3 (1990): 617. http://dx.doi.org/10.1071/ch9900617.

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Reaction of 2-ethoxy-2-methyl-1,3-dioxolan (1c) with 1-methoxy-1-trimethylsilyloxyethene (4a) in dichloromethane in the presence of titanium tetrachloride gave 62% of methyl 2-(2′-methyl-1′,3′-dioxolan-2′-yl)acetate (5a). Similarly, reaction of (1c) with l-methoxy-1-trimethylsilyloxyprop-1-ene (4b) afforded 73% of methyl 2-(2′-methyl-1′,3′-dioxolan-2′-yl) propanoate (5b).
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11

Salman, Yeşim Gül, Ömür Makinabakan, and Levent Yüceer. "Tricyclic ortho ester formation from trichloroethylidene acetals of sugars via ketene acetals." Tetrahedron Letters 35, no. 49 (1994): 9233–36. http://dx.doi.org/10.1016/0040-4039(94)88475-7.

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12

Collins, D. J., M. Dosen, and A. G. Jhingran. "Enolic ortho esters. V.1 Regiospecific generation of diketo ester monoacetals by reaction of an enolic ortho ester with ketene silyl acetals." Tetrahedron Letters 31, no. 3 (1990): 421–22. http://dx.doi.org/10.1016/s0040-4039(00)94571-4.

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13

Iida, Akira, Kenta Takai, Tomohito Okabayashi, Tomonori Misaki, and Yoo Tanabe. "NaOH-catalyzed crossed Claisen condensation between ketene silyl acetals and methyl esters." Chemical Communications, no. 25 (2005): 3171. http://dx.doi.org/10.1039/b504750a.

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14

Liepa, Andris, and Saba Jahangiri. "Organic Lewis Acid Assisted Elimination: Ortho Esters as Surrogates for Ketene Acetals." Synlett 2007, no. 6 (2007): 0939–43. http://dx.doi.org/10.1055/s-2007-973880.

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15

Yang, Junfeng, and Jianrong (Steve) Zhou. "A general method for asymmetric arylation and vinylation of silyl ketene acetals." Org. Chem. Front. 1, no. 4 (2014): 365–67. http://dx.doi.org/10.1039/c4qo00027g.

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16

Takai, Kenta, Yuuya Nawate, Tomohito Okabayashi, Hidefumi Nakatsuji, Akira Iida, and Yoo Tanabe. "Practical and robust method for stereoselective preparations of ketene silyl (thio)acetal derivatives and NaOH-catalyzed crossed-Claisen condensation between ketene silyl acetals and methyl esters." Tetrahedron 65, no. 28 (2009): 5596–607. http://dx.doi.org/10.1016/j.tet.2009.02.084.

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17

Broadhurst, Michael D. "A novel intramolecular ester-enolate alkylation: preparation of acyl ketene acetals." Journal of Organic Chemistry 50, no. 7 (1985): 1117–18. http://dx.doi.org/10.1021/jo00207a040.

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18

Reddy, Chaganti P., та Shigeo Tanimoto. "Reactions of trimethylsilyl ketene acetals with benzoyl cyanide and with α- keto esters". J. Chem. Soc., Perkin Trans. 1, № 2 (1988): 411–14. http://dx.doi.org/10.1039/p19880000411.

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19

Bailey, William J., Jia-Ming Gu, Yin-Nian Lin, Zhi-Feng Zheng, and Lin-Lin Zhou. "Ring-opening polymerization of cyclic ketene acetals and unsaturated cyclic spiro ortho esters." Makromolekulare Chemie. Macromolecular Symposia 42-43, no. 1 (1991): 195–203. http://dx.doi.org/10.1002/masy.19910420116.

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20

Huang, David S, та John F Hartwig. "Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals". Angewandte Chemie 122, № 33 (2010): 5893–97. http://dx.doi.org/10.1002/ange.201002328.

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21

Huang, David S, та John F Hartwig. "Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals". Angewandte Chemie International Edition 49, № 33 (2010): 5757–61. http://dx.doi.org/10.1002/anie.201002328.

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22

Hartwig, J., та D. Huang. "Pd-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals". Synfacts 2010, № 11 (2010): 1283. http://dx.doi.org/10.1055/s-0030-1258723.

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23

Le Engers, Julie, and Brian L. Pagenkopf. "A General Asymmetric Aldol Reaction of Silyl Ketene Acetals Derived from Simple Esters to Aryl α-Keto Esters." European Journal of Organic Chemistry 2009, no. 35 (2009): 6109–11. http://dx.doi.org/10.1002/ejoc.200901086.

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24

Nishi, Takafumi, Isao Mizota, and Makoto Shimizu. "Integrated reactions using addition to conjugated imines and iminium salts." Pure and Applied Chemistry 84, no. 12 (2012): 2609–17. http://dx.doi.org/10.1351/pac-con-12-01-03.

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Recently, nucleophilic addition reactions to imino functions have been utilized in many crucial steps for the synthesis of bioactive and functional materials. This article summarizes the integrated “umpolung” reactions of α-imino esters and the use of iminium salts as reactive electrophiles. Regarding the umpolung reactions, the following five reactions are discussed: (1) N-alkylation/homocoupling; (2) tandem N-ethylation/C-allylation; (3) tandem N-ethylation/C-cyanation; (4) reduction of imines with tris(trimethylsilyl)aluminum; and (5) N-alkylation and Claisen rearrangement. Moreover, the ge
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25

Makioka, Yoshikazu, Yuki Taniguchi, Ken Takaki та Yuzo Fujiwara. "Facile Isomerization of Trimethylsilyl Ketene Acetals to α-Trimethylsilyl Esters Catalyzed by Lanthanoid Trifluoromethanesulfonates". Chemistry Letters 23, № 3 (1994): 645–48. http://dx.doi.org/10.1246/cl.1994.645.

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26

Huang, David S, та John F Hartwig. "Berichtigung: Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals". Angewandte Chemie 122, № 40 (2010): 7310. http://dx.doi.org/10.1002/ange.201090130.

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27

Huang, David S, та John F Hartwig. "Corrigendum: Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals". Angewandte Chemie International Edition 49, № 40 (2010): 7154. http://dx.doi.org/10.1002/anie.201090130.

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28

Shimizu, Makoto. "Unexpected and intriguing reactivity of α-imino esters and iminium salts". Pure and Applied Chemistry 78, № 10 (2006): 1867–76. http://dx.doi.org/10.1351/pac200678101867.

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An intriguing umpolung of the reactivity of imines possessing electron-withdrawing groups was observed. For example, N-alkylation-coupling reaction of the imines derived from glyoxylates was conducted with dialkylaluminum chloride in acetonitrile to give N-monoalkylated 1,2-diamines in good yields. On treatment of various α-imino esters with organoaluminum reagents and allyltributyltin in the presence of benzoyl peroxide (BPO), the tandem reaction proceeded to give the N-alkylation/C-allylation products in good yields. Diethyl 2-[N-(p-methoxyphenyl)imino]-malonate underwent amination reactions
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29

Brittain, William J. "A Review of Group-Transfer Polymerization." Rubber Chemistry and Technology 65, no. 3 (1992): 580–600. http://dx.doi.org/10.5254/1.3538630.

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Abstract Group-transfer polymerization is a very useful synthetic method for the preparation of acrylic ester polymers. This living polymerization process works well at room temperature and can be used to prepare a wide variety of complex polymer structures. Mechanistic work suggests that GTP is a form of anionic polymerization where propagation occurs via a small concentration of enolate anions which are in equilibrium with dormant silyl ketene acetal chain ends. GTP will find the most use in specialty applications including dispersants, toners, photoresists, and rheology control agents.
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30

Mizota, Isao, Shun Agatani, Iwao Hachiya та Makoto Shimizu. "Reductive aminopropylation of ketene silyl (thio)acetals leading to the synthesis of δ-amino esters". Tetrahedron Letters 52, № 41 (2011): 5388–91. http://dx.doi.org/10.1016/j.tetlet.2011.08.054.

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31

Huang, David S., та John F. Hartwig. "ChemInform Abstract: Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals." ChemInform 41, № 50 (2010): no. http://dx.doi.org/10.1002/chin.201050083.

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32

Huang, Zhi-Tang, та Ping-Cheng Zhang. "Synthesis of heterocyclic ketene N,O-Acetals and their reactions with α,β-unsaturated esters". Chemische Berichte 122, № 10 (1989): 2011–16. http://dx.doi.org/10.1002/cber.19891221029.

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33

KATRITZKY, A. R., N. SHOBANA та P. A. HARRIS. "ChemInform Abstract: Preparation of β-Amino Esters from Ketene Silyl Acetals and N-( Alkylamino)benzotriazoles." ChemInform 22, № 37 (2010): no. http://dx.doi.org/10.1002/chin.199137143.

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34

Saigo, Kazuhiko, Shigeru Shimada, Toshifumi Shibasaki, and Masaki Hasegawa. "Lewis Acid-Mediated Reaction of 2,2-Dialkoxycyclopropanecarboxylic Esters with Ketene Silyl Acetals. Synthesis of Cyclopentenones." Chemistry Letters 19, no. 7 (1990): 1093–96. http://dx.doi.org/10.1246/cl.1990.1093.

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35

Li, Bowen, Bangke Luo, Caroline A. Blakemore та ін. "Synthesis of α-Heteroaryl Propionic Esters by Palladium-Catalyzed α-Heteroarylation of Silyl Ketene Acetals". Organic Letters 23, № 16 (2021): 6439–43. http://dx.doi.org/10.1021/acs.orglett.1c02257.

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36

Seitz, Gunther, and Johanna Siegl. "Synthese neuer Pyridin-C-nukleoside der 2 ,3 -Didesoxyribose durch „inverse“ [4+2]-Cycloaddition Synthesis of Novel Pyridine-C-nucleosides of 2,3-Dideoxyribose by „Inverse“ [4+2]-Cycloaddition." Zeitschrift für Naturforschung B 52, no. 7 (1997): 851–58. http://dx.doi.org/10.1515/znb-1997-0715.

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The anomeric imido esters 5 and 6, appropriate precursors for C-nucleoside synthesis, were prepared and utilized as heterodienophiles in a Diels-Alder reaction with inverse electron demand to yield the novel, protected 1.2.4-triazine C-nucleosides 8 and 9. They could be deprotected by treatment with 70% trifluoroacetic acid to furnish the free C-nucleosides 10 and 11. The triazine „aglycon“ of 8 contains an electron deficient diazadiene system, highly activated to react with various electron rich dienophiles such as enamines, enol ethers and several cyclic ketene acetals in an „inverse“ [4+2]-
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37

Saunthwal, Rakesh K., Matthew T. Cornall, Roman Abrams, John W. Ward та Jonathan Clayden. "Connective synthesis of 5,5-disubstituted hydantoins by tandem α-amination and α-arylation of silyl ketene acetals". Chemical Science 10, № 11 (2019): 3408–12. http://dx.doi.org/10.1039/c8sc05263h.

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38

Huang, Zhi-Tang, та Xian Shi. "Synthesis of Heterocyclic KeteneN,S-Acetals and Their Reactions with Esters of α,β-Unsaturated Acids". Synthesis 1990, № 02 (1990): 162–67. http://dx.doi.org/10.1055/s-1990-26822.

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39

Hattori, Kouji, and Hisashi Yamamoto. "Highly selective generation and application of (E)- and (Z)-silyl ketene acetals from .alpha.-hydroxy esters." Journal of Organic Chemistry 58, no. 20 (1993): 5301–3. http://dx.doi.org/10.1021/jo00072a005.

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40

Kise, Naoki, Shinsaku Isemoto та Toshihiko Sakurai. "Electroreductive Coupling of Phthalimides with α,β-Unsaturated Esters: Unusual Rearrangement of Resulting Silyl Ketene Acetals". Organic Letters 11, № 21 (2009): 4902–5. http://dx.doi.org/10.1021/ol902016a.

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41

Gatzenmeier, Tim, Philip S. J. Kaib, Julia B. Lingnau, Richard Goddard та Benjamin List. "The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters". Angewandte Chemie International Edition 57, № 9 (2018): 2464–68. http://dx.doi.org/10.1002/anie.201712088.

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42

MAKIOKA, Y., Y. TANIGUCHI, K. TAKAKI та Y. FUJIWARA. "ChemInform Abstract: Facile Isomerization of Trimethylsilyl Ketene Acetals to α- Trimethylsilyl Esters Catalyzed by Lanthanoid Trifluoromethanesulfonates." ChemInform 25, № 31 (2010): no. http://dx.doi.org/10.1002/chin.199431066.

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43

Iwata, Shin, Toshiyuki Hamura, Takashi Matsumoto, and Keisuke Suzuki. "Mukaiyama Aldol Reaction of Ester Acceptors: Organoaluminums Catalyze Nucleophilic Addition of Ketene Silyl Acetals." Chemistry Letters 36, no. 4 (2007): 538–39. http://dx.doi.org/10.1246/cl.2007.538.

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44

Kavipriya, K., and M. Chandra. "FTIR and GCMS Analysis of Bioactive Phytocompounds in Methonalic Leaf Extract of Cassia Alata." Biomedical and Pharmacology Journal 11, no. 1 (2018): 141–47. http://dx.doi.org/10.13005/bpj/1355.

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The methanolic extract of plant Cassia alata was prepared by using soxhlet apparatus. FTIR and GCMS analysis were done to this plant extract to find out the bioactive phytocompounds. The FTIR results of this plant extract showed 21 peaks indicate the presence of the bioactive compounds such as sulfates, sulfonamides, sulfones, sulfonyl chlorides, sulfates, sulfonamides, alkanes, aromatic, aromatic, alkenes, ester, alkenes, ketenes, isocyanates, isothiocyanates, acetylene, nitrile, phosphine, phosphine, aldehyde, alkane, amide, alcohol and alcohol. The GCMS results showed 13 peaks. The retentio
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45

Tokuyama, Hidetoshi, Hiroyuki Isobe та Eiichi Nakamura. "Photoaddition of silyl ketene acetal to [60]fullerene. Synthesis of α-fullerene-substituted carboxylic esters". J. Chem. Soc., Chem. Commun., № 24 (1994): 2753–54. http://dx.doi.org/10.1039/c39940002753.

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46

Moriarty, Robert M., Neena Rani, Cristian Condeiu, Michael P. Duncan та Om Prakash #. "Hypervalent Iodine Oxidation of Trimethylsilyl Ketene Acetals: A Convenient Route to α-Methoxylation of Esters and Lactones". Synthetic Communications 27, № 18 (1997): 3273–77. http://dx.doi.org/10.1080/00397919708004187.

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47

SAIGO, K., S. SHIMADA, T. SHIBASAKI, and M. HASEGAWA. "ChemInform Abstract: Lewis Acid-Mediated Reaction of 2,2-Dialkoxycyclopropanecarboxylic Esters with Ketene Silyl Acetals. Synthesis of Cyclopentenones." ChemInform 22, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199132124.

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48

Gray, Brian D., та James D. White. "Condensation of ketene acetals derived from glycolates with aldehydes and ketones: synthesis of α,β-dialkoxy esters". J. Chem. Soc., Chem. Commun., № 1 (1985): 20–21. http://dx.doi.org/10.1039/c39850000020.

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49

Adam, Waldemar, and Xiaoheng Wang. "Photooxygenation of silyl ketene acetals: dioxetanes as precursors to .alpha.-silylperoxy esters in the silatropic ene reaction." Journal of Organic Chemistry 56, no. 15 (1991): 4737–41. http://dx.doi.org/10.1021/jo00015a030.

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50

Hiraguri, Yoichi, Kenichi Katase, and Yutaka Tokiwa. "Biodegradability of Poly(ester‐ether) and Poly(ester) Obtained from a Radical Ring‐Opening Polymerization of Cyclic Ketene Acetals." Journal of Macromolecular Science, Part A 42, no. 7 (2005): 901–7. http://dx.doi.org/10.1081/ma-200063155.

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