Synthesis of 2-functionalized allyl tris(trimethylsilyl)silanes

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6383-6386

  Chatgilialoglu, Chryssostomos ^a   Ballestri, Marco ^a   Vecchi, Donatella ^a   Curran, Dennis P ^b  

^a CNR   (Italy)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030603048     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01353-6     Document Type: Article

References (28)

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3. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4; pp. 715-831.
4. (d) Curran, D. P. Synthesis 1988, 489.
5. 2. For the initial development of this reaction, see: (a) Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
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11. (e) Padwa, A.; Murphree, S. S.; Yeske, P. E. Tetrahedron Lett. 1990, 31, 2983.
12. (f) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738.
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16. 4. For reviews, see: (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
17. (b) Chatgilialoglu, C.; Ferreri, C. Res. Chem. Intermed. 1993, 19, 755.
18. (c) Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229.
19. 3Si• radicals are known to add reversibly to a variety of double bonds and, therefore, to isomerize alkenes, see: Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
20. 2Br gave an unseparable mixture of two isomer (1:1 ratio) and, therefore was abandoned.
21. 2Br under free radical conditions giving poor yields, see: Kosugi, M.; Kurata, H.; Kawata, K.; Migita, T. Chem. Lett. 1991, 1327.
22. -1 at room temperature, depending on the stabilizing effect of the Z group. For a review on thiyl radicals, see: Chatgilialoglu, C.; Guerra, M. In Supplement S: The chemistry of sulphur-containing functional groups; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1993; pp 363-394.
23. (b) For a review on sulfonyl radicals, see: Chatgilialoglu, C. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; pp 1081-1113.
24. +), 345, 287, 259, 229, 191, 147, 73, 45.
25. 3SiH with S-O bonds will be reported separately.
26. 11. Apparently (based on BDEs) the reaction 5 for Y = PhS is expected to be inefficient. For an explanation, see: Zavitsas, A. A.; Chatgilialoglu, C. J. Am. Chem. Soc. 1995, 117, 10645.
27. 12. Chatgilialoglu, C.; Gilbert, B. C.; Kirk, C. M.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1979, 1084.
28. 13. For a review, see: Bravermann, S. In The chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; pp 665-716.