"Front Matter". In: Organosilanes in Radical Chemistry - Index of
"Front Matter". In: Organosilanes in Radical Chemistry - Index of "Front Matter". In: Organosilanes in Radical Chemistry - Index of
References 115 In connection with the above procedure, Co(III)-alkyl and Co(III)-alkylperoxo complexes were found to catalyse triethylsilylperoxidation of alkenes with O2 and Et3SiH (Reaction 5.50). Although the proposed radical chain mechanism does not involve Et3SiOO: radical, this species is believed to play a role in the initiation step [94]. RCo(III) or OOSiEt ROOCo(III) 3 (5.50) R' + Et3SiH + O2 R' (TMS) 3SiH and poly(hydrosilane)s show autoxidation to form polysiloxanes. 18 O-Labelling experiments with (TMS)3SiH and (TMS) 2MeSiH allowed for envisaging an operating mechanism that involves consecutive rearrangements (see Sections 6.5 and 8.2 for details). The addition of silyl radicals to P w S and P Se bonds have been used for w synthetic purposes. A variety of silicon hydrides react with Ph3P S by a radical w chain mechanism to give the corresponding silanethiols in good yields (Reaction 5.51) [95]. The reaction mechanism is similar to the reaction of silanes with O w C S reported in Scheme 5.12. The intermediate phosphoranyl adduct 61 was identified w by EPR and the data obtained suggest that the unpaired electron reside in the PS s orbital. (TMS) 3SiH reacts with phosphine sulfides and phosphine selenides under free-radical conditions to give the corresponding phosphines in good yields [96]. The initial step of these reactions is the addition of (TMS) 3Si: radical to P w SandP Se bonds. For details and stereochemical w studies on P-chiral compounds, see Section 4.3.4. 5.7 REFERENCES Ph3P=S + R3SiH Ph3P + R3SiSH Ph 3P S Si(OCMe3) 3 61 (5.51) 1. Sommer, L.H., Pietrusza, E.W., and Whitmore, F.C., J. Am. Chem. Soc., 1947, 69, 188. Burkhard, C.A., and Krieble, R.H., J. Am. Chem. Soc., 1947, 69, 2687. Barry, A.J., De Pree, L., Gilkey, J.W., and Hook, D.E., J. Am. Chem. Soc., 1947, 69, 2916. 2. Comprehensive Handbook on Hydrosilylation, B. Marciniec, (Ed.), Pergamon, Oxford, 1992. 3. El-Durini, N.M.K., and Jackson, R.A., J. Organomet. Chem., 1982, 232, 117. 4. Speier, J.L., Adv. Organomet. Chem., 1979, 17, 407. 5. Ojima, I. In The Chemistry of Organic Silicon Compounds, S. Patai and Z. Rappoport (Eds), Wiley, Chichester, 1989, pp. 1479–1526. 6. Ojima, I., Li, Z., and Zhu, J. In The Chemistry of Organic Silicon Compounds, Volume 2, Z. Rappoport and Y. Apeloig (Eds), Wiley, Chichester, 1998, pp. 1687–1792. 7. Marciniec, B., Silicon Chem., 2002, 1, 155.
116 Addition to Unsaturated Bonds 8. Sakurai, H. In Free Radicals, Volume II, J.K. Kochi (Ed.), Wiley, New York, 1973, pp. 741–808. 9. Alberti, A., and Pedulli, G.F., Rev. Chem. Intermed., 1987, 8, 207. 10. Dohmaru, T. In Chemical Kinetics of Small Organic Radicals, Volume III, Z.B. Alfassi (Ed.), CRC Press, Boca Raton, FL, 1988, pp. 165–195. 11. Sakurai, H., Kyushin, S., Nakadaira, Y., and Kira, M., J. Phys. Org. Chem., 1988, 1, 197. 12. Guerra, M., J. Am. Chem. Soc., 1992, 114, 2077. 13. Chatgilialoglu, C., Ingold, K.U., and Scaiano, J.C., J. Am. Chem. Soc., 1983, 105, 3292. 14. Lusztyk, J., Maillard, B., and Ingold, K.U., J. Org. Chem., 1986, 51, 2457. 15. Ballestri, M., Chatgilialoglu, C., Clark, K.B., Griller, D., Giese, B., and Kopping, B., J. Org. Chem., 1991, 56, 678. 16. Arthur, N.L., and Potzinger, P., Organometallics, 2002, 21, 2874. 17. Lozano, A.E., Alonso, A., Catalina, F., and Peinado, C., Macromol. Theory Simul., 1999, 8, 93. 18. Jackson, R.A., J. Chem. Soc., Chem. Commun., 1974, 573. 19. Chatgilialoglu, C., Ballestri, M., Ferreri, C., and Vecchi, D., J. Org. Chem., 1995, 60, 3826. 20. Chatgilialoglu, C., Altieri, A., and Fischer, H., J. Am. Chem. Soc., 2002, 124, 12816. 21. Griller, D., Marriott, P.R., Nonhebel, D.C., Perkins, M.J., and Wong, P.C., J. Am. Chem. Soc., 1981, 103, 7761. 22. Kira, M., Sugiyama, H., and Sakurai, H., J. Am. Chem. Soc., 1983, 105, 6436. 23. Lunazzi, L., Placucci, G., and Grossi, L., J. Chem. Soc., Perkin Trans. 2, 1982, 875. 24. Chatgilialoglu, C., Ingold, K.U., Lusztyk, J., Nazran, A.S., and Scaiano, J.C., Organometallics, 1983, 2, 1332. 25. Kopping, B., Chatgilialoglu, C., Zehnder M., and Giese, B., J. Org. Chem., 1992, 57, 3994. 26. Smadja, W., Zahouily, M., and Malacria, M., Tetrahedron Lett., 1992, 33, 5511. 27. Roberts, B.P., Chem. Soc. Rev., 1999, 28, 25. 28. Dang, H.-S., and Roberts, B.P., Tetrahedron Lett., 1995, 36, 2875. 29. Smadja, W., Zahouily, M., Journet, M., and Malacria, M., Tetrahedron Lett., 1991, 32, 3683. 30. Haque, M.B., and Roberts, B.P., Tetrahedron Lett., 1996, 37, 9123. 31. Haque, M.B., Roberts, B.P., and Tocher, D.A. J. Chem. Soc., Perkin Trans. 1, 1998, 2881. 32. Du, W., Kaskar, B., Blumbergs, P., Subramanian, P.-K., and Curran, D.P., Bioorg. Med. Chem., 2003, 11, 451. 33. Chatgilialoglu, C., Ballestri, M., Vecchi, D., and Curran, D.P., Tetrahedron Lett., 1996, 37, 6383. 34. Amrein, S., and Studer, A., Helv. Chim. Acta, 2002, 85, 3559. 35. Matsumoto, A., and Ito, Y., J. Org. Chem., 2000, 65, 5707. 36. Wiberg, K.B., and Waddell S.T., J. Am. Chem. Soc., 1990, 112, 2184. 37. Scaiano, J.C., and McGarry, P.F., Can. J. Chem., 1998, 76, 1474. 38. Chatgilialoglu, C., and Ferreri, C. In Supplement C2: The Chemistry of Triple- Bonded Functional Groups, S. Patai (Ed.), Wiley, Chichester, 1994, pp. 917–944. 39. Miura, K., Oshima, K., and Utimoto, K., Bull. Chem. Soc. Jpn., 1993, 66, 2356. 40. Gilman, H., and Wittenberg, D., J. Org. Chem., 1958, 23, 501. 41. Hudson, A., and Jackson, R.A., Chem. Commun., 1969, 1323. 42. Fischer, H., and Paul, H. In Magnetic Properties of Free Radicals, H. Fischer and K.-H. Hellwege (Eds) Landolt–Börnstein New Series, Volume II/9b, Springer, Berlin, 1977.
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116 Addition to Unsaturated Bonds<br />
8. Sakurai, H. <strong>In</strong> Free <strong>Radical</strong>s, Volume II, J.K. Kochi (Ed.), Wiley, New York, 1973,<br />
pp. 741–808.<br />
9. Alberti, A., and Pedulli, G.F., Rev. Chem. <strong>In</strong>termed., 1987, 8, 207.<br />
10. Dohmaru, T. <strong>In</strong> Chemical K<strong>in</strong>etics <strong>of</strong> Small Organic <strong>Radical</strong>s, Volume III, Z.B.<br />
Alfassi (Ed.), CRC Press, Boca Raton, FL, 1988, pp. 165–195.<br />
11. Sakurai, H., Kyush<strong>in</strong>, S., Nakadaira, Y., and Kira, M., J. Phys. Org. Chem., 1988, 1,<br />
197.<br />
12. Guerra, M., J. Am. Chem. Soc., 1992, 114, 2077.<br />
13. Chatgilialoglu, C., <strong>In</strong>gold, K.U., and Scaiano, J.C., J. Am. Chem. Soc., 1983, 105,<br />
3292.<br />
14. Lusztyk, J., Maillard, B., and <strong>In</strong>gold, K.U., J. Org. Chem., 1986, 51, 2457.<br />
15. Ballestri, M., Chatgilialoglu, C., Clark, K.B., Griller, D., Giese, B., and Kopp<strong>in</strong>g,<br />
B., J. Org. Chem., 1991, 56, 678.<br />
16. Arthur, N.L., and Potz<strong>in</strong>ger, P., Organometallics, 2002, 21, 2874.<br />
17. Lozano, A.E., Alonso, A., Catal<strong>in</strong>a, F., and Pe<strong>in</strong>ado, C., Macromol. Theory Simul.,<br />
1999, 8, 93.<br />
18. Jackson, R.A., J. Chem. Soc., Chem. Commun., 1974, 573.<br />
19. Chatgilialoglu, C., Ballestri, M., Ferreri, C., and Vecchi, D., J. Org. Chem., 1995, 60,<br />
3826.<br />
20. Chatgilialoglu, C., Altieri, A., and Fischer, H., J. Am. Chem. Soc., 2002, 124, 12816.<br />
21. Griller, D., Marriott, P.R., Nonhebel, D.C., Perk<strong>in</strong>s, M.J., and Wong, P.C., J. Am.<br />
Chem. Soc., 1981, 103, 7761.<br />
22. Kira, M., Sugiyama, H., and Sakurai, H., J. Am. Chem. Soc., 1983, 105, 6436.<br />
23. Lunazzi, L., Placucci, G., and Grossi, L., J. Chem. Soc., Perk<strong>in</strong> Trans. 2, 1982, 875.<br />
24. Chatgilialoglu, C., <strong>In</strong>gold, K.U., Lusztyk, J., Nazran, A.S., and Scaiano, J.C.,<br />
Organometallics, 1983, 2, 1332.<br />
25. Kopp<strong>in</strong>g, B., Chatgilialoglu, C., Zehnder M., and Giese, B., J. Org. Chem., 1992, 57,<br />
3994.<br />
26. Smadja, W., Zahouily, M., and Malacria, M., Tetrahedron Lett., 1992, 33, 5511.<br />
27. Roberts, B.P., Chem. Soc. Rev., 1999, 28, 25.<br />
28. Dang, H.-S., and Roberts, B.P., Tetrahedron Lett., 1995, 36, 2875.<br />
29. Smadja, W., Zahouily, M., Journet, M., and Malacria, M., Tetrahedron Lett., 1991,<br />
32, 3683.<br />
30. Haque, M.B., and Roberts, B.P., Tetrahedron Lett., 1996, 37, 9123.<br />
31. Haque, M.B., Roberts, B.P., and Tocher, D.A. J. Chem. Soc., Perk<strong>in</strong> Trans. 1, 1998,<br />
2881.<br />
32. Du, W., Kaskar, B., Blumbergs, P., Subramanian, P.-K., and Curran, D.P., Bioorg.<br />
Med. Chem., 2003, 11, 451.<br />
33. Chatgilialoglu, C., Ballestri, M., Vecchi, D., and Curran, D.P., Tetrahedron Lett.,<br />
1996, 37, 6383.<br />
34. Amre<strong>in</strong>, S., and Studer, A., Helv. Chim. Acta, 2002, 85, 3559.<br />
35. Matsumoto, A., and Ito, Y., J. Org. Chem., 2000, 65, 5707.<br />
36. Wiberg, K.B., and Waddell S.T., J. Am. Chem. Soc., 1990, 112, 2184.<br />
37. Scaiano, J.C., and McGarry, P.F., Can. J. Chem., 1998, 76, 1474.<br />
38. Chatgilialoglu, C., and Ferreri, C. <strong>In</strong> Supplement C2: The <strong>Chemistry</strong> <strong>of</strong> Triple-<br />
Bonded Functional Groups, S. Patai (Ed.), Wiley, Chichester, 1994, pp. 917–944.<br />
39. Miura, K., Oshima, K., and Utimoto, K., Bull. Chem. Soc. Jpn., 1993, 66, 2356.<br />
40. Gilman, H., and Wittenberg, D., J. Org. Chem., 1958, 23, 501.<br />
41. Hudson, A., and Jackson, R.A., Chem. Commun., 1969, 1323.<br />
42. Fischer, H., and Paul, H. <strong>In</strong> Magnetic Properties <strong>of</strong> Free <strong>Radical</strong>s, H. Fischer and<br />
K.-H. Hellwege (Eds) Landolt–Börnste<strong>in</strong> New Series, Volume II/9b, Spr<strong>in</strong>ger,<br />
Berl<strong>in</strong>, 1977.
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