Chemoselectivity of the [2+3]-Cycloaddition of Thiocarbonyl Ylides with 5-Benzylidene-3-phenylrhodanine

• Autorzy: Seyfried M. , Linden A. , Mlostoń G. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

Reactions of three different thiocarbonyl S-methylides, generated from thiobenzophenone (2), 2,2,4,4-tetramethyl-3-thioxocyclobutanone (3), and adamantanethione (8), respectively, and diazomethane, with 5-benzylidene-3-phenylrhodanine (12) were carried out. The aromatic thiocarbonyl ylide 1a adds chemoselectively to the C,C-double bond, but the spirocyclic 1,3-dithiolane 18, i.e. the [2+3]-cycloadduct with the C=S group of 12,was also formed as a minor product. In the cases of the aliphatic thiocarbonyl ylides 6 and 20, the [2+3]-cycloaddition occurred at the exocyclic C,C-double bond exclusively to give the spirocyclic tetrahydrothiophene derivatives 23 and 21, respectively. Asmooth acid-catalyzed decomposition of 18 yielded the 2-diphenylmethylidene derivative 19. The formation of product 24, which was obtained in the reaction of the sterically congested ylide 6 with 12, is explained by a 1,4-H-shift in an intermediate zwitterionic adduct. The structures of the tetrahydrothiophenes 17, 21 and 23, as well as that of 24, were established by X-ray crystallography.

Słowa kluczowe

EN

thiocarbonyl ylides; 1,3-dipolar cycloaddition; rhodanine; 2,5-dihydro-1,3,4-thiadiazoles; crystal structure

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2006
• Tom: Vol. 80, nr 8
• Strony: 1363--1376
• Opis fizyczny: Bibliogr. 49 poz., rys.

Twórcy

autor

Seyfried M.

autor

Linden A.

autor

Mlostoń G.

autor

Heimgartner H.

• Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Bibliografia

• 1.Huisgen R., Angew. Chem. Int. Ed. Engl., 2,565 (1963); Huisgen R., Angew. Chem. Int. Ed. Engl., 2,633 (1963).
• 2.Huisgen R., in '1,3-Dipolar Cycloaddition Chemistry', ed. Padwa, A., Vol. l, Wiley, New York, 1984, p.1.
• 3.Huisgen R., The Adventure Playground of Mechanisms andNovel Reactions', Ed. Seeman J.T., American Chemical Society, Washington, D.C., 1994.
• 4.a) Staudinger H. and Gaule A., Ber. Dtsch. Chem. Ges., 49,1897 and 1951 (1916); b) Staudinger H. And Siegwart J., Helv. Chim. Acta, 3, 833 (1920).
• 5.a) Schönberg A. and Vargha L., Liebigs Ann. Chem., 483, 176 (1930); b) Schönberg A. and Vargha L., Ber. Dtsch. Chem. Ges., 64,1390 (1931); c) Schönberg A., Cernik D. and Urban W., Ber. Dtsch. Chem. Ges., 64,2577 (1931); d) Schönberg A., Nickel S. and CemikD., Ber. Dtsch. Chem. Ges., 65,289 (1932).
• 6.Huisgen R., Fulka C., Kalwinsch I., Li, X., Mlostoń G., Rodriguez Moran J. and Probstl A., Bull. Soc. Chim. Belg.,93,511(1984).
• 7.Huisgen R., Langhals E., Mlostoń G., Oshima T. and Rapp J., Lectures in Heterocycl. Chem., 9, S-1 (1987).
• 8.a) Huisgen R., Fisera L., Giera H. and Sustmann R., J. Am. Chem. Soc., 117,9671 (1995); b) Sustmann R., Sicking W. and Huisgen R., J. Am .Chem. Soc., 117, 9678 (1995).
• 9. Huisgen R., Li X., Giera H. and Langhals E., Helv. Chim. Acta, 84, 981 (2001).
• 10.Huisgen R. and Langhals E., Tetrahedron Lett., 30, 5369 (1989).
• 11.Huisgen R. and Li X., Tetrahedron Lett., 24, 4185 (1983).
• 12.Mlostoń G. and Heimgartner H., Polish J. Chem., 74, 1503 (2000).
• 13.Mlostoń G. and Heimgartner H., in The Chemistry of Heterocyclic Compounds', Vol. 59: 'Synthetic Applications of l ,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products', Eds. Padwa A. and Pearson W.H., Wiley, New York, 2002, p. 315.
• 14.Huisgen R., Kalwinsch L, Li X. and Mlostoń G., Eur. J. Org. Chem., 1685 (2000).
• 15.Huisgen R., Li X., Mlostoń G. and Fulka C., Eur. J. Org. Chem., 1695 (2000).
• 16.Urbaniak K., Mlostoń G., Gulea M., Masson S., Linden A. and Heimgartner H., Eur. J. Org. Chem., 1604 (2005).
• 17.Mlostoń G., Linden A. and Heimgartner H., Helv. Chim. Acta, 74, 1386 (1991).
• 18.Huisgen R. and Mlostoń G., Heterocycles, 23, 2201 (1985).
• 19.Aono M., Terao Y. and Achiwa K., Chem. Lett., 1851 (1987).
• 20.Huisgen R., Mlostoń G. and Fulka C., Heterocycles, 23, 2207 (1985).
• 21.Buchel T., Prewo R., Bieri J. H. and Heimgartner H., Helv. Chim. Acta, 67, 534 (1984).
• 22. a) Kagi M., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 79, 855 (1996); b) Kagi M., Mlostoń G., Linden A. and Heimgartner H., Helv. Chim. Acta, 77, 1299 (1994); c) Petit M., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 77,1076 (1994); d) Kagi M., Linden A., Heimgartner H. and Mlostoń G., Helv. Chim. Acta, 76, 1715 (1993).
• 23. a) Gebert A., Linden A., Mlostoń G. and Heimgartner H., Heterocycles, 56, 393 (2002); b) Mlostoń G.,Linden A. and Heimgartner H., Helv. Chim. Acta, 81, 558 (1998); c) Mlostoń G., Linden A. and Heimgartner H., Polish J. Chem., 71, 32 (1997).
• 24.Meier K.-R., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 80, 1190 (1997).
• 25.Fisera L., Jaroskova L., Matejkova I. and Heimgartner H., Heterocycles, 40, 271 (1995).
• 26.a) Hassaneen H.M., Shawali A.S., Fargas D.S. and Ahmed, E.M., Phosphorus, Sulfur and Silicon, 113, 53 (1996); b) Linden A.,Awad E.M.A.H. and Heimgartner H., Acta Crystallogr., Sect. C, 55, 1877 (1999).
• 27.Awad E.M.A.H. and Heimgartner H., unpublished.
• 28.Andreasch R. and Zipser A., Monatsh. Chem., 24, 499 (1903).
• 29.Johnson C.K., 'ORTEP II', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
• 30.Seyfried M.S., Linden A. and Heimgartner H., in preparation.
• 31.Malaschichin S., Fu C., Linden A. and Heimgartner H., Helv. Chim. Acta, 88, 3253 (2005).
• 32.Mlostoń G., Janicka E., Woznicka M., Linden A. and Heimgartner H., PolishJ. Chem., 77,1805 (2003).
• 33.Huisgen R., MIostoń G., Giera H. and Langhals E., Tetrahedron, 58, 507 (2002).
• 34.a) Polshetiwar V. and Kaushik M. P., Tetrahedron Lett., 45, 6255 (2004); b) Köster R. and Seidel G., Z. Naturforsch. B, 43, 687 (1988).
• 35.Greidanus J.W., Can. J. Chem., 48, 350 (1970).
• 36.a) Majchrzak A., Janczak, A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 86, 2272 (2003); b) Elam E. U. and Davis H. R, J. Org. Chem., 32, 1562 (1967).
• 37.Heimgartner H. and Mlostoń G., in 'Electronic Encyclopedia of Reagents in Organic Synthesis', Eds. Paquette L., Rigby J., Crich D. and Wipf R, J. Wiley & Sons, Chichester UK, Article RN00429.
• 38.Heimgartner H., Mlostoń G. and Romański J., in 'Electronic Enzyclopedia of Reagents in Organic Synthesis', Eds. Paquette L., Rigby J., Crich D. and Wipf P, J. Wiley & Sons, Chichester UK, Article RN00504.
• 39.Hooft R.,KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
• 40.Otwinowski Z. and Minor W, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. Carter C.W., Jr. and Sweet R.M., Academic Press, New York, 1997, p. 307.
• 41.Blessing R.H., Acta Crystallogr., Sect. A, 51, 33 (1995).
• 42.Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G. and Camalli M., SIR92, J. Appl. Crystallogr., 27, 435 (1994).
• 43.Spek A.L., PLATON, Program for the Analysis of Molecular Geometry, University of Utrecht, The Netherlands, 2005.
• 44. Beurskens P.T., Admiraal G., Beurskens G., Bosman W.P., Garcia-Granda S., Gould R.O., Smits J.M.M. and Smykalla C., PATTY: The DIRDIFprogram system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.
• 45. Beurskens P.T., Admiraal, G., Beurskens G., Bosman W.P, de Gelder R., Israel R. and Smits J.M.M.,DIRDIF94: The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
• 46. a) Maslen E.N., Fox A.G. and O'Keefe M.A., in 'International Tables for Crystallography', Ed. Wilson A.J.C., Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6. l. l. l, p. 477; b) Creagh D.C. and McAuley W.J., ibld., Table4.2.6.8, p. 219; c) Creagh D.C. andHubbell J.H., ibid., Table4.2.4.3, p. 200.
• 47.Stewart R.F., Davidson E.R. and Simpson W.T., J. Chem. Phys., 42, 3175 (1965).
• 48.Ibers J.A. and Hamilton W.C., Acta Crystallogr., 11, 781 (1964).
• 49.Sheldrick G.M., SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.