A novel and efficient method for the preparation of asymmetric dithioacetals
作者： J.Y. Gauthier , T. Henien , L. Lo , M. Thérien , R.N. Young
DOI: 10.1016/S0040-4039(00)82440-5
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摘要: Abstract Aldehydes and ketones react with one equivalent each of thiols thiolacetic acid under catalysis to yield almost exclusively the mixed alkylthio-(or arylthio-) acylthioacetals. Reaction thioacetal a nucleophile (such as NaOMe) liberates thiolate anion which can be trapped variety electrophiles provide asymmetric dithioacetals in high yields.
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Carl D. Perchonock, Mary E. McCarthy, Karl F. Erhard, John G. Gleason, Martin A. Wasserman, Roseanna M. Muccitelli, Jeris F. DeVan, Stephanie S. Tucker, Lynne M. Vickery, Synthesis and pharmacological characterization of 5-(2-dodecylphenyl)-4,6-dithianonanedioic acid and 5-[2-(8-phenyloctyl)phenyl]-4,6-dithianonanedioic acid: prototypes of a novel class of leukotriene antagonists Journal of Medicinal Chemistry. ,vol. 28, pp. 1145- 1147 ,(1985) , 10.1021/JM00147A004
Paul Dubs, Rita Stüssi, Investigation of the Head‐Space of Roasted Meat II. Synthesis of substituted 2, 4, 5‐trithia‐hexanes Helvetica Chimica Acta. ,vol. 61, pp. 2351- 2359 ,(1978) , 10.1002/HLCA.19780610708
Anil K. Saksena, Michael J. Green, Pietro Mangiaracina, Jesse K. Wong, William Kreutner, Arax R. Gulbenkian, Synthesis of butanoic acid 4,4′-[(4E, 6Z, 9Z-pentadecatrien-2-ynylidene)-bis with leukotriene- like activity: Novel acetylenic acetals and dithioacetals as antagonists of leukotriene-C4 Tetrahedron Letters. ,vol. 26, pp. 6427- 6430 ,(1985) , 10.1016/S0040-4039(00)99018-X
Jacques Yves Gauthier, France Bourdon, Robert Norman Young, A mild and efficient synthesis of thiolesters from alcohols Tetrahedron Letters. ,vol. 27, pp. 15- 18 ,(1986) , 10.1016/S0040-4039(00)83927-1
Theodor Posner, Zur Kenntniss der Disulfone. XII. Ueber gemischte Disulfone Berichte der deutschen chemischen Gesellschaft. ,vol. 36, pp. 296- 304 ,(1903) , 10.1002/CBER.19030360165
Lothar Kistenbrügger, Jürgen Voß, Elektroreduktion organischer Verbindungen, 2. Darstellung von Dithioacetalen durch alkylierende Elektroreduktion von Dithiocarbonsäureestern European Journal of Organic Chemistry. ,vol. 1980, pp. 472- 480 ,(1980) , 10.1002/JLAC.198019800316
H. Böhme, H. Bezzenberger, G. Müller, Alkyl‐ und Aryl‐acyl‐derivate geminaler Dithiole Archiv Der Pharmazie. ,vol. 306, pp. 268- 271 ,(1973) , 10.1002/ARDP.19733060405
Yvan Guindon, Richard Frenette, Rejean Fortin, Joshua Rokach, Direct synthesis of thio ethers from thiols and alcohols Journal of Organic Chemistry. ,vol. 14, pp. 1357- 1359 ,(1983) , 10.1021/JO00156A043