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Nonenforced concerted general-acid catalysis of the dehydration step in formaldehyde thiosemicarbazone formation

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    Nonenforced concerted general-acid catalysis of the dehydration step in formaldehyde thiosemicarbazone formation
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    Cite this: J. Am. Chem. Soc. 1980, 102, 21, 6466–6472
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    https://doi.org/10.1021/ja00541a015
    Published October 8, 1980
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    This article is cited by 16 publications.

    1. F. Terrier,, M. Sebban,, R. Goumont,, J. C. Hallé,, G. Moutiers,, I. Cangelosi, and, E. Buncel. Dual Behavior of 4-Aza-6-nitrobenzofuroxan. A Powerful Electrophile in Hydration and σ-Complex Formation and a Potential Dienophile or Heterodiene in Diels−Alder Type Reactions. The Journal of Organic Chemistry 2000, 65 (22) , 7391-7398. https://doi.org/10.1021/jo0005114
    2. Sirinan Kulchat, Manuel N. Chaur, Jean‐Marie Lehn. Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry. Chemistry – A European Journal 2017, 23 (46) , 11108-11118. https://doi.org/10.1002/chem.201702088
    3. Clara Eugenia Baños, Manuel Silva. A novel clean-up method for urine analysis of low-molecular mass aldehydes by capillary electrophoresis with laser-induced fluorescence detection. Journal of Chromatography B 2011, 879 (17-18) , 1412-1418. https://doi.org/10.1016/j.jchromb.2010.10.033
    4. Mieczysław Ziełiński, Marianna Kańska. Syntheses and Uses of Isotopically Labelled Compounds Containing C  C , C  O or C  N Groups. 2009https://doi.org/10.1002/9780470682531.pat0134
    5. Silvana Azzolini Travalon, Inês Maria Costa Brighente, Rosendo Augusto Yunes. Spontaneous dehydration mechanism of aromatic aldehyde reactions with hydroxyl and non‐hydroxyl amines. International Journal of Chemical Kinetics 2002, 34 (12) , 685-692. https://doi.org/10.1002/kin.10095
    6. Sergio Duvoisin Junior, Carlos A. Kuhnen, Ines C.M. Brighente, Rosendo A. Yunes. Theoretical study of electronic and steric effects in the dehydration step of norcanphor and substituted norcanphor. Journal of Molecular Structure: THEOCHEM 1998, 427 (1-3) , 229-235. https://doi.org/10.1016/S0166-1280(97)00242-X
    7. Jacir Dalmagro, Rosendo A. Yunes, Edesio Luiz Simionatto. Mechanism of reaction of azobenzene formation from aniline and nitrosobenzene in basic conditions. General base catalysis by hydroxyide ion. Journal of Physical Organic Chemistry 1994, 7 (8) , 399-402. https://doi.org/10.1002/poc.610070803
    8. Ines Maria Costa Brighente, Leonor Rosa Vottero, Alberto Jose Terezani, Rosendo Augusto Yunes. Steric and Electronic Effects on the Dehydration Step in Cyclohexanone and Bicyclic Ketones Oxime Formation. Bulletin of the Chemical Society of Japan 1993, 66 (8) , 2289-2293. https://doi.org/10.1246/bcsj.66.2289
    9. Isabel M. Plaza del Pino, Juan Llor, Jose M. Sanchez-Ruiz. Kinetics of the formation and hydrolysis of the Schiff's base of pyridoxal 5′-phosphate with hexylamine in water–dioxane. J. Chem. Soc., Perkin Trans. 2 1993, 96 (3) , 581-584. https://doi.org/10.1039/P29930000581
    10. Michael W. Washabaugh, Charles C. Yang, James T. Stivers, Kyung-Sang Lee. Mechanism of hydrolysis of a thiazolium ion: General acid-base catalysis of the breakdown of the tetrahedral addition intermediate. Bioorganic Chemistry 1992, 20 (4) , 296-312. https://doi.org/10.1016/0045-2068(92)90040-A
    11. Edward J. Crane, Michael W. Washabaugh. General acid catalysis of the cleavage of 2-(1-hydroxybenzyl)thiamin by a preassociation mechanism. Bioorganic Chemistry 1991, 19 (4) , 351-368. https://doi.org/10.1016/0045-2068(91)90019-L
    12. Roseane Fett, Edésio L. Simionatto, Rosendo A. Yunes. General‐acid, specific‐base and intramolecular catalysis of the dehydration step in nitrone formation from furfurals and phenylhydroxylamine. Journal of Physical Organic Chemistry 1990, 3 (9) , 620-626. https://doi.org/10.1002/poc.610030911
    13. Juan Llor, Salvador Asensio, Jose Manuel Sanchez‐ruiz. Kinetics of the formation and hydrolysis of the schiff's base of 4‐pyridinecarboxaldehyde with N ‐hexylamine in water‐dioxan mixtures. International Journal of Chemical Kinetics 1989, 21 (1) , 51-61. https://doi.org/10.1002/kin.550210105
    14. G. Lamaty, J.P. Roque, A. Natat, T. Silou. Reaction d'oximation des cetones iv.. Tetrahedron 1986, 42 (10) , 2657-2666. https://doi.org/10.1016/S0040-4020(01)90551-4
    15. G. Lamaty, J.P. Roque, A. Natat, T. Silou. Reactions d'oximation des cetones V. Mecanisme et effets de structure dans la reaction de deshydratation acido-catalysee des carbinolamines. Tetrahedron 1986, 42 (10) , 2667-2676. https://doi.org/10.1016/S0040-4020(01)90552-6
    16. J. L. PALMER, W. P. JENCKS. ChemInform Abstract: NONENFORCED CONCERTED GENERAL‐ACID CATALYSIS OF THE DEHYDRATION STEP IN FORMALDEHYDE THIOSEMICARBAZONE FORMATION. Chemischer Informationsdienst 1981, 12 (3) https://doi.org/10.1002/chin.198103139
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 1980, 102, 21, 6466–6472
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja00541a015
    Published October 8, 1980
    Request reuse permissions

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