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Journal articles on the topic 'Hydrogenolysis. Acetates'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 February 2022

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1

Belmont, James A., Jorge Soto, Roswell E. King, Andrew J. Donaldson, John D. Hewes, and M. Frederick Hawthorne. "Metallacarboranes in catalysis. 8. I: Catalytic hydrogenolysis of alkenyl acetates. II: Catalytic alkene isomerization and hydrogenation revisited." Journal of the American Chemical Society 111, no. 19 (1989): 7475–86. http://dx.doi.org/10.1021/ja00201a031.

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2

Robins, Morris J., Ruiming Zou, Fritz Hansske, and Stanislaw F. Wnuk. "Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymatic deamination with adenosine deaminase." Canadian Journal of Chemistry 75, no. 6 (1997): 762–67. http://dx.doi.org/10.1139/v97-092.

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Treatment of 2,6-diaminopurine riboside (2-aminoadenosine) with α-acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2′,3′-bromohydrin acetates 2. Treatment of 2 with zinc–copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a). Treatment of 2 with Dowex 1 × 2 (OH−) resin in methanol gave the 2′,3′-anhydro derivative 4. Stannyl radical-mediated hydrogenolysis of 2 and deprotection gave the 2′-deoxy 6a and 3′-deoxy 7a nucleosides. Treatment of the 3′,5′-O-(tetraisopropyldisiloxanyl) derivative (

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3

Tsuji, Jiro, Ichiro Minami, and Isao Shimizu. "Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-Triethylamine." Synthesis 1986, no. 08 (1986): 623–27. http://dx.doi.org/10.1055/s-1986-31723.

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4

Agarwal, A. K., N. W. Cant, M. S. Wainwright, and D. L. Trimm. "Catalytic hydrogenolysis of esters: a comparative study of the reactions of simple formates and acetates over copper on silica." Journal of Molecular Catalysis 43, no. 1 (1987): 79–92. http://dx.doi.org/10.1016/0304-5102(87)87023-2.

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5

Gozlan, Charlotte, Elsa Deruer, Marie-Christine Duclos, et al. "Preparation of amphiphilic sorbitan monoethers through hydrogenolysis of sorbitan acetals and evaluation as bio-based surfactants." Green Chemistry 18, no. 7 (2016): 1994–2004. http://dx.doi.org/10.1039/c5gc02131f.

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6

Xu, Rui, Kunbo Lian, Zhikang Xu, et al. "Controllable synthesis of Ir(Rh)–Sn/SiO2 bimetallic catalysts via surface organometallic chemistry for the production of ethanol from hydrogenolysis of ethyl acetate." Catalysis Science & Technology 10, no. 4 (2020): 1086–95. http://dx.doi.org/10.1039/c9cy02071c.

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A series of highly active Ir–Sn/SiO<sub>2</sub> and Rh–Sn/SiO<sub>2</sub> catalysts for ethyl acetate hydrogenolysis to ethanol were prepared from the grafting synthesis based on the surface organometallic chemistry concept.

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7

Burns, CJ, M. Gill, and S. Saubern. "Pigments of Fungi. XXI. Synthesis of (±)-6-Demethoxyaustrocortirubin." Australian Journal of Chemistry 44, no. 10 (1991): 1427. http://dx.doi.org/10.1071/ch9911427.

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6-Demethoxyaustrocortirubin (6) is synthesized via the epoxide (21) which is available in 73% yield over four steps from naphthazarin (10). Hydrolysis of the epoxide (21) yields the diol (25) which on hydrogenolysis affords 6-demethoxy-1-deoxyaustrocortirubin (7). Stereoselective benzylic hydroxylation of (7) gives (6). Cleavage of the epoxide (21) with sodium acetate in acetic acid affords a mixture of the esters (22)-(24), while methanolysis yields the isomeric ethers (29) and (30). Hydrogenolysis of (22), (23) and (29) gives high yields of (7). Potentially more direct routes to the alcohol

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8

Perich, JW, RM Valerio, PF Alewood, and RB Johns. "Synthesis of Casein Related Peptides and Phosphopeptides. XIV. Solid Phase Synthesis of Glu-Ser(P)-Leu Through the Use of Protected Boc-Ser(PO3R2)-OH Derivatives." Australian Journal of Chemistry 44, no. 6 (1991): 771. http://dx.doi.org/10.1071/ch9910771.

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A solid phase method is described for the synthesis of O- phosphoseryl-containing peptides by the use of polystyrene resin (Merrifield) as the peptide support and protected Boc-Ser(PO3R2)-OH derivatives for the incorporation of the phosphorylated seryl residue. The viability of this solid phase approach was demonstrated by the synthesis of HBr.H-Glu-Ser (PO3Et2)-Leu-OH in high yield by the use of Bo -Ser(PO3Et2)-OH in peptide synthesis and subsequent use of HBr/CF3CO2H for cleavage of the Ser(PO3Et2)-containing tripeptide from the resin support. Similarly, the dipeptide, CF3CO2H.H-Ser(P)- Leu

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9

Kadyrov, Renat. "Hydrogenolysis of Amide Acetals and Iminium Esters." ChemCatChem 10, no. 1 (2017): 170–72. http://dx.doi.org/10.1002/cctc.201701287.

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10

Rajagopal, S., and A. F. Spatola. "Palladium-catalyzed transfer hydrogenolysis of benzyl acetate with ammonium formate." Applied Catalysis A: General 152, no. 1 (1997): 69–81. http://dx.doi.org/10.1016/s0926-860x(96)00342-0.

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11

Xu, Zichen, Honghui Gong, Manyu Chen, et al. "Catalytic hydrogenolysis of glycerol into propyl acetate with ruthenium complexes." Catalysis Communications 129 (September 2019): 105743. http://dx.doi.org/10.1016/j.catcom.2019.105743.

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12

Borbás, Anikó, János Hajkó, Mária Kajtár-Peredy, and András Lipták. "Hydrogenolysis of Dioxolane-Type Diphenylmethylene Acetals by AlClH2to Axial Diphenylmethyl Ethers." Journal of Carbohydrate Chemistry 12, no. 2 (1993): 191–200. http://dx.doi.org/10.1080/07328309308021269.

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13

Antczak, Kazimierz, John F. Kingston, and Alex G. Fallis. "Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene: a general intramolecular Diels–Alder approach to tricyclic sesquiterpenes." Canadian Journal of Chemistry 63, no. 4 (1985): 993–95. http://dx.doi.org/10.1139/v85-166.

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Stereoselective total synthesis of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl)-2-pentenoate 11 affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (12) which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function (Ph3P/CCl4/CH3CN; H2/Pd/C), reduc

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14

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides." Australian Journal of Chemistry 69, no. 1 (2016): 61. http://dx.doi.org/10.1071/ch15445.

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Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]tri

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15

Antczak, Kazimierz, John F. Kingston, Alex G. Fallis, and Alfred W. Hanson. "A general intramolecular Diels–Alder approach to tricyclic sesquiterpenes: stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene." Canadian Journal of Chemistry 65, no. 1 (1987): 114–23. http://dx.doi.org/10.1139/v87-019.

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Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl-2-pentenoate 13c affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (14c), which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function by elimination and hydrogenatio

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16

Zhang, Kun, Xing-Long Li, Shi-Yan Chen, Hua-Jian Xu, Jin Deng, and Yao Fu. "Selective Hydrogenolysis of Furfural Derivative 2-Methyltetrahydrofuran into Pentanediol Acetate and Pentanol Acetate over Pd/C and Sc(OTf)3 Cocatalytic System." ChemSusChem 11, no. 4 (2018): 726–34. http://dx.doi.org/10.1002/cssc.201702073.

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17

van de Scheur, F. "Structure-activity relation and ethane formation in the hydrogenolysis of methyl acetate on silicasupported copper catalysts." Applied Catalysis A: General 111, no. 1 (1994): 63–77. http://dx.doi.org/10.1016/0926-860x(94)80067-7.

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18

Vincent, Aurélie, and Joëlle Prunet. "Selective hydrogenolysis of benzyl ethers in the presence of benzylidene acetals with Raney nickel." Tetrahedron Letters 47, no. 24 (2006): 4075–77. http://dx.doi.org/10.1016/j.tetlet.2006.03.189.

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19

Tararov, Vitali I., Renat Kadyrov, Thomas H. Riermeier, and Armin Börner. "Synthesis of N-(Dialkylaminoalkyl)alcohols by Homogeneously Catalyzed Hydrogenolysis of Cyclic N,O-Acetals." Synthesis 2002, no. 03 (2002): 375–80. http://dx.doi.org/10.1055/s-2002-20039.

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20

Latypova, Adel R., Olga V. Lefedova, Dmitry V. Filippov, and Valentin Yu Doluda. "FEATURES OF HYDROGENIZATION OF 2-CHLORO-4-NITROANILINE ON SUPPORTED PALLADIUM AND PLATINUM CATALYSTS IN 2-PROPANOL AND ETHYL ACETATE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 1 (2019): 86–91. http://dx.doi.org/10.6060/ivkkt.20206301.5983.

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The article is devoted to studying the solvent and catalyst nature influence on the 2-chloro-4-nitroaniline hydrogenation kinetic regularities on supported palladium and platinum catalysts in an aqueous solution of azeotropic composition and ethyl acetate. It is known that the halogen-substituted nitrobenzenes reduction may be accompanied by a secondary stage of hydrogenolysis. In this regard, the development of objective ideas about the selective control methods of the studied reaction the transformations staging is an extremely important task. The paper discusses the influence of the solvent

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21

Bieg, Tadeusz, and Wiesław Szeja. "Catalytic-transfer hydrogenolysis of benzylidene acetals with palladium-carbon and ammonium formate or hydrazine hydrate." Carbohydrate Research 154, no. 1 (1986): 296–300. http://dx.doi.org/10.1016/s0008-6215(00)90044-2.

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22

Moreau, Claude, Jérôme Lecomte, Samir Mseddi, and Najib Zmimita. "Stereoelectronic effects in hydrolysis and hydrogenolysis of acetals and thioacetals in the presence of heterogeneous catalysts." Journal of Molecular Catalysis A: Chemical 125, no. 2-3 (1997): 143–49. http://dx.doi.org/10.1016/s1381-1169(97)00083-6.

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23

Tararov, Vitali I., Renat Kadyrov, Thomas H. Riermeier, and Armin Boerner. "ChemInform Abstract: Synthesis of N-(Dialkylaminoalkyl)alcohols by Homogeneously Catalyzed Hydrogenolysis of Cyclic N,O-Acetals." ChemInform 33, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200224084.

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24

Claus, Peter, Martin Lucas, Bernhard Lücke, Torsten Berndt, and Peter Birke. "Selective hydrogenolysis of methyl and ethyl acetate in the gas phase on copper and supported Group VIII metal catalysts." Applied Catalysis A: General 79, no. 1 (1991): 1–18. http://dx.doi.org/10.1016/0926-860x(91)85002-f.

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25

Sajiki, Hironao. "Selective inhibition of benzyl ether hydrogenolysis with Pd/C due to the presence of ammonia, pyridine or ammonium acetate." Tetrahedron Letters 36, no. 20 (1995): 3465–68. http://dx.doi.org/10.1016/0040-4039(95)00527-j.

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26

Ma, Dawei, Wengen Wu та Ping Deng. "Facile synthesis of (+)-α-allokainic acid via Pd-catalyzed hydrogenolysis of allyl acetate derived from trans-4-hydroxy-l-proline". Tetrahedron Letters 42, № 39 (2001): 6929–31. http://dx.doi.org/10.1016/s0040-4039(01)01440-x.

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27

Liu, Yanyong, Kazuhisa Murata, Megumu Inaba, and Isao Takahara. "Synthesis of ethanol from methanol and syngas through an indirect route containing methanol dehydrogenation, DME carbonylation, and methyl acetate hydrogenolysis." Fuel Processing Technology 110 (June 2013): 206–13. http://dx.doi.org/10.1016/j.fuproc.2012.12.016.

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28

Borbás, Anikó, Zoltán B. Szabó, László Szilágyi, Attila Bényei, and András Lipták. "Stereoselective (2-naphthyl)methylation of sugar hydroxyls by the hydrogenolysis of diastereoisomeric dioxolane-type (2-naphthyl)methylene acetals." Carbohydrate Research 337, no. 21-23 (2002): 1941–51. http://dx.doi.org/10.1016/s0008-6215(02)00180-5.

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29

Fujisawa, Tamotsu, Ryuuichirou Hayakawa та Makoto Shimizu. "Hydrogenolysis-Isomerization-Reduction of Propargyl Acetate, and Regio- and Stereoselective Hydrogenation of Dienyl Ester for the Synthesis of 1β-Methylcarbapenem Precursor". Chemistry Letters 24, № 11 (1995): 1013–14. http://dx.doi.org/10.1246/cl.1995.1013.

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30

SAJIKI, H. "ChemInform Abstract: Selective Inhibition of Benzyl Ether Hydrogenolysis with Pd/C Due to the Presence of Ammonia, Pyridine, or Ammonium Acetate." ChemInform 26, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199536071.

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31

Borbás, Anikó, Gabriella Szabovik, and András Lipták. "Synthesis and hydrogenolysis of dioxolane type diphenylmethylene and fluoren-9-ylidene carbohydrate acetals containing a neighbouring substituted hydroxyl function." Carbohydrate Polymers 34, no. 4 (1997): 430. http://dx.doi.org/10.1016/s0144-8617(97)87367-5.

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32

Jakab, Zsolt, Attila Mándi, Anikó Borbás, et al. "Synthesis, regioselective hydrogenolysis, partial hydrogenation, and conformational study of dioxane and dioxolane-type (9′-anthracenyl)methylene acetals of sugars." Carbohydrate Research 344, no. 18 (2009): 2444–53. http://dx.doi.org/10.1016/j.carres.2009.09.007.

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33

Ma, Dawei, Wengen Wu та Ping Deng. "ChemInform Abstract: Facile Synthesis of (+)-α-Allokainic Acid via Pd-Catalyzed Hydrogenolysis of Allyl Acetate Derived from trans-4-Hydroxy-L-proline." ChemInform 33, № 1 (2010): no. http://dx.doi.org/10.1002/chin.200201200.

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34

Hajkó, János, Anikó Borbás, Gabriella Szabovik, Mária Kajtár-Peredy, and András Lipták. "Synthesis and Hydrogenolysis of Dioxolane-Type Diphenyl-Methylene and Fluoren-9-Ylidene Carbohydrate Acetals Containing a Neighbouring Substituted Hydroxyl Function." Journal of Carbohydrate Chemistry 16, no. 7 (1997): 1123–44. http://dx.doi.org/10.1080/07328309708005742.

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35

FUJISAWA, T., R. HAYAKAWA та M. SHIMIZU. "ChemInform Abstract: Hydrogenolysis-Isomerization-Reduction of Propargyl Acetate, and Regio- and Stereoselective Hydrogenation of Dienyl Ester for the Synthesis of 1β-Methylcarbapenem Precursor." ChemInform 27, № 15 (2010): no. http://dx.doi.org/10.1002/chin.199615273.

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36

Lipták, András, Anikó Borbás, Lóránt Jánossy, and László Szilágyi. "Preparation of (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 2-naphthylmethyl (NAP) ethers." Tetrahedron Letters 41, no. 25 (2000): 4949–53. http://dx.doi.org/10.1016/s0040-4039(00)00735-8.

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37

HAJKO, J., A. BORBAS, G. SZABOVIK, M. KAJTAR-PEREDY, and A. LIPTAK. "ChemInform Abstract: Synthesis and Hydrogenolysis of Dioxolane-Type Diphenylmethylene and Fluoren-9-ylidene Carbohydrate Acetals Containing a Neighboring Substituted Hydroxyl Function." ChemInform 29, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.199804200.

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38

Lipták, András, Zoltán Szurmai, V. Anna Oláh, János Harangi, Lajos Szabó та Pál Nánási. "Synthesis and hydrogenolysis of the methylene, ethylidene, isopropylidene, and diastereoisomeric 1-phenylethylidene acetals of β-l-arabino- and α-l-rhamnopyranoside derivatives". Carbohydrate Research 138, № 1 (1985): 1–15. http://dx.doi.org/10.1016/0008-6215(85)85218-6.

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39

Lipták, András, Anikó Borbás, Lóránt Jánossy, and László Szilágyi. "Corrigendum to “Preparation of (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 2-naphthylmethyl (NAP) ethers”." Tetrahedron Letters 41, no. 43 (2000): 8397. http://dx.doi.org/10.1016/s0040-4039(00)01450-7.

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40

Hajkó, János, Anikó Borbás, András Lipták, and Mária Kajtár-Peredy. "Preparation of dioxolane-type fluoren-9-ylidene acetals of carbohydrates and their hydrogenolysis with AlClH 2 to give axial fluoren-9-yl ethers." Carbohydrate Research 216 (September 1992): 413–20. http://dx.doi.org/10.1016/0008-6215(92)84177-t.

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41

Ledvina, Miroslav, Daniel Zyka, Jan Ježek, Tomáš Trnka та David Šaman. "New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity". Collection of Czechoslovak Chemical Communications 63, № 4 (1998): 577–89. http://dx.doi.org/10.1135/cccc19980577.

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Ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (5), prepared by benzylation of ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), was transformed by reaction with bromine into 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (6). Thioglycoside 5 in the presence of methyl triflate and glycosylbromide 6 in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (7), to give benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-p

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42

Borbás, Anikó, Zoltán B. Szabó, László Szilágyi, Attila Bényei, and András Lipták. "Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers." Tetrahedron 58, no. 28 (2002): 5723–32. http://dx.doi.org/10.1016/s0040-4020(02)00515-x.

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43

YAO, ZhiLong. "Effect of calcium and boron modified on the structure and hydrogenolysis performance of CuO/Al<sub>2</sub>O<sub>3</sub> in catalyzing sec-butyl acetate." SCIENTIA SINICA Chimica 44, no. 1 (2014): 114–20. http://dx.doi.org/10.1360/032013-238.

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44

BELMONT, J. A., J. SOTO, R. E. III KING, A. J. DONALDSON, J. D. HEWES, and M. F. HAWTHORNE. "ChemInform Abstract: Metallacarboranes in Catalysis. Part 8. Catalytic Hydrogenolysis of Alkenyl Acetates. Catalytic Alkene Isomerization and Hydrogenation Revisited." ChemInform 21, no. 1 (1990). http://dx.doi.org/10.1002/chin.199001059.

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45

TSUJI, J., I. MINAMI, and I. SHIMIZU. "ChemInform Abstract: Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-triethylamine." Chemischer Informationsdienst 17, no. 52 (1986). http://dx.doi.org/10.1002/chin.198652111.

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46

LIPTAK, A., and Z. SZURMAI. "ChemInform Abstract: Reactions of Carbohydrate Acetals. Part 2. Hydrogenolysis of Acetals." Chemischer Informationsdienst 17, no. 42 (1986). http://dx.doi.org/10.1002/chin.198642352.

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47

Vincent, Aurelie, and Joelle Prunet. "Selective Hydrogenolysis of Benzyl Ethers in the Presence of Benzylidene Acetals with Raney Nickel." ChemInform 37, no. 39 (2006). http://dx.doi.org/10.1002/chin.200639062.

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48

BIEG, T., and W. SZEJA. "ChemInform Abstract: Catalytic-Transfer Hydrogenolysis of Benzylidene Acetals with Palladium-Carbon and Ammonium Formate or Hydrazine Hydrate." ChemInform 18, no. 18 (1987). http://dx.doi.org/10.1002/chin.198718330.

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49

LIPTAK, A., Z. SZURMAI, V. A. OLAH, J. HARANGI, L. SZABO та P. NANASI. "ChemInform Abstract: SYNTHESIS AND HYDROGENOLYSIS OF THE METHYLENE, ETHYLIDENE, ISOPROPYLIDENE, AND DIASTEREOISOMERIC 1-PHENYLETHYLIDENE ACETALS OF β-L-ARABINO- AND α-L-RHAMNOPYRANOSIDE DERIVATIVES". Chemischer Informationsdienst 16, № 37 (1985). http://dx.doi.org/10.1002/chin.198537299.

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