Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Addition of Thiols to Sulfonylacetylenes: Synthetic Applications Rocío Medel, Joaquin Plumet*Departamento de Química Organica I, Facultad de Química, Universidad Complutense, 28040 Madrid, SpainFax: +34(91)3944100; e-Mail: plumety@quim.ucm.es; Recommend Article Abstract Buy Article All articles of this category Abstract The addition of propane-1,3-dithiol to p-toluenesulfonylacetylene affords the dithioacetal 1. This compound is a useful building block for the synthesis of new functionalized sulfanylvinylsulfonyl derivatives. Key words dithioacetals - base-induced - ring-opening - S-alkylation - sulfanylvinylsulfonyl derivatives Full Text References References 1a Stirling CJM. J. Chem. Soc. 1964, 5856 1b For a review on the chemistry of acetylenic and allenic sulfones, see: Back TG. Tetrahedron 2001, 57: 5263 ; the addition of thiols, sulfinates and related nucleophiles is considered in pp 5276-5277 2 Selling HA. Tetrahedron 1975, 31: 2387 3 Tichenor GJW. Truce WE. J. Org. Chem. 1972, 37: 2391 4a Arjona O. Iradier F. Medel R. Plumet J. J. Org. Chem. 1999, 64: 6090 4b Arjona O. Medel R. Rojas JK. Costa AM. Vilarrasa J. Tetrahedron Lett. 2003, 44: 6369 5 Medel R. Monterde MI. Plumet J. Rojas JK. J. Org. Chem. 2005, 70: 735 For the synthesis of oxathianes and dithianes by stereoselective addition-cyclization of hydroxythiols and dithiols to electron-poor acetylenes, see: 6a De Lucci O. Marchioro C. Modena G. Lucchini V. Tetrahedron Lett. 1985, 26: 4539 6b De Lucci O. Marchioro C. Modena G. Lucchini V. Valle G. J. Org. Chem. 1986, 51: 1457 For the synthesis of acyclic and the cyclic thioacetal 5 (Figure 2) by base-catalyzed addition of ethanedithiol to arylsulfonylacetylenes, see: 6c Buso M. De Lucci O. Modena G. Tetrahedron Lett. 1987, 28: 107 6d Cossu S. De Lucci O. Fabris F. Ballini R. Bosica G. Synthesis 1996, 1481 7 The reaction of propane-1,3-dithiol and p-toluenesulfonylacetylene in presence of Me3P (THF) affords a mixture of compounds 6 and 7 (mixture of diastereomers) (Figure [3] ). Figure 3 Compounds 6 and 7 8 Kruse CG. Janse ACV. Dert V. Van der Gen A. J. Org. Chem. 1979, 44: 2916 9 Marshal JA. Sertz DE. J. Org. Chem. 1975, 40: 534 10a Hase TA. Latineen L. Tetrahedron Lett. 1981, 22: 3285 10b Hase TA. Latineen L. J. Organomet. Chem. 1982, 240: 9 11 Mroskowski C. Manna S. Falck JR. Tetrahedron Lett. 1984, 25: 519 12 Simpkins NS. Sulphones in Organic Synthesis Pergamon; London: 1993.
