Download e-book for iPad: Advances in Sulfur Chemistry, Volume 2 by C.M. Rayner
By C.M. Rayner
This quantity is a testomony to the continued significance of sulfur chemistry, and the large development that has been made in recent times.
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The loss of the olefin 76 results in the thione 78 via the enethiolate 77. The phenyl group migrates from the silicon to the adjacent carbon, giving the thiolate 79 which, by Michael addition to the olefin 76, affords product 74 after desilylation (Scheme 50). R\ ^ S j Ni(PPh3)2Cl2 55 R2 Si Si 71 60-94% R^ = Et, Ph Si = SiMes, SiMeaPh R2=Me, Et, Bu Scheme 47. ^R2 . ^v R\ AorB . 55 S R2 ^ ^ ^ V ^ 73 R^ = Et, hPr, Ph SI = SIMe2Ph, SiMes R 2 = H . 3 Scheme 48. ^\_/^-^--EWG ^SiMesPh _IBAF__ THF/H2OA p Ph 1^ "^ ' ^EWG 74 48-60% EWG = COOEt, COOMe, CN, COMe Scheme 49.
Janzen, E. ; Haire, D. L. Adv. Free Radical Chem. 1990,1, 253. 70. Scaiano, J. C ; Ingold, K. U. / Am. Chem. Soc 1976, 98, 4727. 71. ; Colonna, F R; Pedulli, G. F Tetrahedron 1980, 36, 3043. 72. Adeleke, B. ; Chen, K. ; Wan, J. K. S. / Organomet. Chem. 1981, 208, 317. 73. S. Phosphorus Sulphur 1984, 21, 135. 74. ; Bonini, B. F ; Pedulli, G. F Tetrahedron Lett. 1987, 28, 3737. 75. ; Bonini, B. F ; Pedulli, G. F J. Chem. Soc, Faraday Trans. 1 1988, 84, 3347. 76. ; Stella, L. Ace Chem. Res. 1985,18, 917.
Organomet. Chem. 1992,434, 151. 16. Bonini, B. ; Zani, R; Maccagnani, G. J. Chem. Soc, Perkin Trans. 1 1989, 2083. 17. Bonini, B. ; Zani, R J. Chem. Soc, Chem. Commun. 1988, 365. 18. Bonini, B. ; Ricci, A. Tetrahedron 1996, 52, 4803. 19. ; Reginato, G. J. Org. Chem. 1989, 54,19. 20. Bonini, B. ; Ricci, A. Synlett. In press. 21. ; Bongini, A. Tetrahedron 1989,45, 5137. 22. ; Perry, D. A. J. Am. Chem. Soc 1983,105, 6999. 23. ; Giorgianni, P. J. Chem. Soc, Perkin Trans. 11987, 2647. 24. Bonini, B.
Advances in Sulfur Chemistry, Volume 2 by C.M. Rayner