A convergent synthesis of γ-unsaturated thioaldehyde-and thioketone-S-oxides

Bulletin de la Societe Chimique de France

Volumn 133, Issue 5, 1996, Pages 515-529

  Baudin, Jean Bernard ^a   Commenil, Marie Gabrielle ^a   Julia, Sylvestre A ^a   Wang, Yuan ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

1,2 dithietane 1,1 dioxide; 3.3 sigmatropic rearrangement; Elimination; Grignard reaction; Unsaturated sulfinic ester; Unsaturated sulfoxide; Unsaturated thioaldehyde s oxide; Unsaturated thioketone s oxide; Z alkene

Indexed keywords

EID: 0010751995     PISSN: 00378968     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (47)

1. For reviews on the chemistry of sulfines, see: a) Duus F, in Comprehensive Organic Chemistry, Barton DHR, Ollis WD, Neville-Jones D, Eds. Pergamon, Oxford, 1979, Vol 3, p 409
2. b) Block E, in Organic Sulfur Chemistry, 9th International Symposium on Organic Sulfur Chemistry, Riga, USSR, 9-14 June 1980, Freidlina RKh, Skorova AE Eds, Pergamon, Oxford, 1981, pp 15-34
3. c) Zwanenburg B, Recl Trav Chim Pays-Bas (1982) 101, 1
4. d) Zwanenburg B, Lenz BG, in Houben-Weyl Methoden der Organischen Chemie, George Thieme, Stuttgart, 1985, Band E11, p 911
5. e) Zwanenburg B, Phosphorus, Sulfur and Silicon (1989) 43, 1
6. Braverman S, Grinstein D, Gottlieb HE, Tetrahedron Lett (1994) 35, 953
7. a) Van Der Leij M, Zwanenburg B, Tetrahedron Lett (1978), 3383
8. b) Porskamp PATW, Van de Wijdeven AM, Zwanenburg B, Recl Trav Chim Pays-Bas (1983) 102, 506
9. Schaumann E, Behz H, Adiwidjaja G, Tangerman A, Lammerink BHM, Zwanenburg B, Tetrahedron (1981) 37, 219
10. a) Block E, Ahmad S, J Am Chem. Soc (1985) 107, 6731
11. b) Block E, Ahmad S, Catalfamo JL, Jain MK, Apitz-Castro R, J Am Chem Soc (1986) 108, 7045
12. a) For the first examples of thio-Claisen rearrangements of non-aromatic alkenyl allyl sulfoxides see Bell R, Cottam PD, Davies J, Neville Jones D, Meanwell NA, Tetrahedron Lett (1980) 21, 4379
13. b) Garigipati RS, Cordova R, Parvez M, Weinreb SM, Tetrahedron (1986) 42, 2979
14. c) Hwu JR, Anderson DA, Tetrahedron Lett (1986) 27, 4965;
15. Hwu JR, Anderson DA, J Chem Soc, Perkin Trans I (1991), 3199
16. d) Mukherjee A, Schulman EM, Le Noble WJ, J Org Chem (1992) 57, 3120
17. Baudin JB, Commenil MG, Julia SA, Wang Y, Synlett (1992) 909
18. Baudin JB, Commenil MG, Julia SA, Toupet L, Wang Y, Synlett (1993) 839
19. Baudin JB, Julia SA, Tetrahedron Lett (1988) 29, 3251;
20. Baudin JB, Julia SA, Tetrahedron Lett (1989) 30, 1963;
21. Bull Soc Chim Fr (1995) 132, 196
22. Block E, Bazzi AA, Revelle LK, J Am Chem Soc (1980) 102, 2490
23. Kempe T, Norin T, Acta Chem Scand Ser B (1974) 28, 613
24. Julia M, Lauron H, Stacino JP, Verpeaux JN, Jeannin Y, Dromzee Y, Tetrahedron (1986) 42, 2475
25. a) Baudin JB, Hareau G, Julia SA, Ruel O, Bull Soc Chim Fr (1993) 130, 336
26. b) Baudin JB, Hareau G, Julia SA, Lorne R, Ruel O, ibidem (1993) 130, 856
27. c) Analogous zwitterions have been postulated for explaining some reactions of sulfur dioxide with olefinic compounds: Masilamani D, Manahan EH, Vitrone J, Rogic MR, J Org Chem (1983) 48, 4918
28. Baudin JB, Julia SA, Wang Y, Synlett (1992) 911;
29. Bull Soc Chim Fr (1995) 132, 952
30. Concerning the reaction of but-2-enylmagnesium chloride with (-) menthyl toluenesulfinate, cf ref 13 in: Bickart P, Carson FW, Jacobus J, Miller EG, Mislow K, J Am Chem Soc (1968) 90, 4869
31. a) Block E, Revelle LK, Bazzi AA, Tetrahedron Lett (1980) 1277
32. b) Barbaro G, Battaglia A, Giorgianni P, Bonini BF, Maccagnani G, Zani P, J Org Chem (1990) 55, 3744
33. Tangerman A, Zwanenburg B, Tetrahedron Lett (1973) 79;
34. J Chem Soc, Perkin Trans 2 (1975) 352;
35. Recl Tr Chim Pays-Bas (1977) 96, 196
36. 4Cl work-up and is comparable with the PPTS-catalyzed tautomerization of some allylthiosulfines to vinylsulfenic acids followed by an intramolecular addition of sulfenic acid to the allylic bond: Mazzanti G, Van Helvoirt E, van Vliet LA, Ruinaard R, Masiero S, Bonini BF, Zwanenburg B, J Chem Soc, Perkin Trans 1 (1994) 3299. For the thermal formation of transient vinylsulfenic acids from sulfines, see ref 6a
37. We thank a referee for suggesting a reasonable path for explaining the formation of thiophene compounds 16, 19. For other dihydrothiophene S-oxides, see Mansuy D, Valadon P, Erdelmeier I, Lopez-Garcia P, Amar C, Girault J-P, Dansette PM, J Am Chem Soc (1991) 113, 7825 and references cited therein
38. Braverman S, Van Asten PFTM, Van Der Linden JB, Zwanenburg B, Tetrahedron Lett (1991) 32, 3867
39. Brandsma L, Verkruijsse HD, Recl Trav Chim Pays-Bas (1974) 93, 319
40. On standing at room temperature, some thioketone S-oxides were converted into the corresponding ketones: Le Nocher AM, Metzner P, Tetrahedron Lett (1991) 32, 747
41. Block E, Yencha AJ, Aslam M, Eswarakrishnan V, Luo J, Sano A, J Am Chem Soc (1988) 110, 4748
42. Hasserodt J, Pritzkow H, Sundermeyer W, Liebigs Ann Chem (1995) 95
43. Barnard D, Cole EP, Anal Chim Acta (1959) 20, 540
44. Chan MM, Kice JL, J Org.Chem (1978) 43, 914
45. Baudin JB, Julia SA, Wang Y, Bull Soc Chim Fr (1995) 132, 739
46. Scholtz D, Liebigs Ann Chem (1984) 259
47. Holler T, Carlin KJ, Büchi G, Organic Synthesis, Coll Vol VII, 517