The reaction of phenyliodonium bis(phenylsulfonyl)methylide with alkyl iodides

Synlett

Volumn , Issue 14, 2004, Pages 2563-2565

  Gogonas, Efstathios P ^a   Nyxas, Ioannis ^a   Hadjiarapoglou, Lazaros P ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

Author keywords

Alkyliodonium ylide; C I insertion; Iodide; Ylide

Indexed keywords

ALKYL GROUP; BETA DISULFONYLIODONIUM YLIDE; IODIDE; IODINE DERIVATIVE; METHYL GROUP; PHENYL GROUP; PHENYLIODONIUMBIS(PHENYLSULFONYL)METHYLIDE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CYCLOADDITION; DECOMPOSITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 9644303111     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834797     Document Type: Article

References (43)

1. Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983, Chap. 18.
2. (a) Doyle, M. P. Chem. Rev. 1986, 86, 919.
3. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
4. (c) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
5. (d) Adams, J.; Spero, D. Tetrahedron 1991, 47, 1765.
6. (e) Ye, T.; Mc Kervey, A. Chem. Rev. 1994, 94, 1091.
7. (f) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
8. (a) Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947.
9. (b) Müller, P.; Baud, C.; Naegeli, I. J. Phys. Org. Chem. 1998, 11, 597.
10. (c) Müller, P.; Bolea, C. Synlett 2000, 826.
11. (d) Camacho, M. B.; Clark, A. E.; Liebrecht, T. A.; DeLuka, J. P. J. Am. Chem. Soc. 2000, 112, 5210.
12. (e) Müller, P.; Bolea, C. Molecules 2001, 6, 258.
13. (f) Müller, P.; Bolea, C. Helv. Chim. Acta 2001, 84, 1093.
14. (g) Georgakopoulou, G.; Kalogiros, C.; Hadjiarapoglou, L. P. Synlett 2001, 1843.
15. (h) Müller, P.; Bolea, C. Helv. Chim. Acta 2002, 85, 483.
16. (i) Batsila, C.; Kostakis, G.; Hadjiarapoglou, L. P. Tetrahedron Lett. 2002, 43, 5997.
17. (a) Moriarty, R. M.; Prakash, O.; Vaid, R. K.; Zhao, L. J. Am. Chem. Soc. 1989, 111, 6443.
18. (b) Moriarty, R. M.; Kim, J.; Guo, L. Tetrahedron Lett. 1993, 34, 4129.
19. (c) Spyroudis, S.; Tarantili, P. J. Org. Chem. 1993, 58, 4885.
20. (d) Moriarty, R. M.; May, E. J.; Prakash, O. Tetrahedron Lett. 1997, 38, 4333.
21. (e) Moriarty, R. M.; May, E. J.; Guo, L.; Prakash, O. Tetrahedron Lett. 1998, 39, 765.
22. (f) Alexiou, I.; Gogonas, E. P.; Hadjiarapoglou, L. P. Synlett 1999, 1925.
23. (g) Gogonas, E. P.; Hadjiarapoglou, L. P. Tetrahedron Lett. 2000, 41, 9299.
24. (a) Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. J. Am. Chem. Soc. 1985, 107, 7178.
25. (b) Hadjiarapoglou, L. P. Ph.D. Dissertation; Aristotelian University of Thessaloniki: Greece, 1987.
26. (c) Hadjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. J. Chem. Soc., Perkin Trans. 1 1988, 2839.
27. (a) Dieckmann, J. J. Org. Chem. 1965, 30, 2272.
28. (b) Klages, F.; Bott, K. Chem. Ber. 1964, 97, 735.
29. Sander, W.; Strehl, A.; Winkler, M. Eur. J. Org. Chem. 2001, 3771.
30. Hadjiarapoglou, L.; Varvoglis, A. Synthesis 1988, 913.
31. Hadjiarapoglou, L.; Varvoglis, A. J. Chem. Soc., Perkin Trans. 1 1989, 379.
32. Adam, W.; Bosio, S.; Gogonas, E. P.; Hadjiarapoglou, L. P. Synthesis 2002, 2084.
33. Adam, W.; Gogonas, E. P.; Hadjiarapoglou, L. P. J. Org. Chem. 2003, 68, 9155.
34. Adam, W.; Gogonas, E. P.; Hadjiarapoglou, L. P. Eur. J. Org. Chem. 2003, 1064.
35. 2 (516.4): C, 46.52; H, 4.10; S, 12.42. Found: C, 46.52; H, 4.07; S, 12.39.
36. Olah, G. A.; Doggweiler, H.; Feiberg, J. D. J. Am. Chem. Soc. 1985, 707, 4975.
37. (a) Moriarty, R. M.; Bailey, B. R. III; Prakash, O.; Prakash, I. J. Am. Chem. Soc. 1985, 107, 1375.
38. (b) Yang, R.-Y.; Dai, L.-X.; Chem, C. G. J. Chem. Soc., Chem. Commun. 1992, 1487.
39. (c) Sheppard, W. A.; Webster, Q. W. J. Am. Chem. Soc. 1973, 95, 2695.
40. Adam, W.; Gogonas, E. P.; Hadjiarapoglou, L. P. Synlett 2003, 1165.
41. Black, K. A.; Vogel, P. J. Org. Chem. 1986, 57, 5341.
42. Lautens, M.; Mancuso, J. Org. Lett. 2002, 4, 2105.
43. Hadjiarapoglou, L.; Varvoglis, A. J. Chem. Res., Synop. 1988, 306.