NMR spectra of phenoxysilanes with various silyl groups

Journal of Organometallic Chemistry

Volumn 521, Issue 1-2, 1996, Pages 157-162

  Hudrlik, Paul F ^a   Minus, Donald K ^a  

^a HOWARD UNIVERSITY   (United States)

Author keywords

NMR spectra; Phenoxysilanes; Silicon

Indexed keywords

EID: 0030598802     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06324-3     Document Type: Article

References (78)

1. [1] E.W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981 (revised edition Krieger Press, Malabar, FL, 1985); E.W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, London, 1988.
2. [1] E.W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981 (revised edition Krieger Press, Malabar, FL, 1985); E.W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, London, 1988.
3. [2] For reviews, see M. Lalonde and T.H. Chan, Synthesis, (1985) 817-845; J.R. Hwu and N. Wang, Chem. Rev., 89 (1989) 1599-1615;
4. [2] For reviews, see M. Lalonde and T.H. Chan, Synthesis, (1985) 817-845; J.R. Hwu and N. Wang, Chem. Rev., 89 (1989) 1599-1615;
5. J. Muzart, Synthesis, (1993) 11-27.
6. [3] For example, see M.A. Brook, C. Henry, R. Jueschke and P. Modi, Synlett, (1993) 97-104; C. Dallaire and M.A. Brook, Organometallics, 12 (1993) 2332-2338; H. Mayr and G. Gorath, J. Am. Chem. Soc., 117 (1995) 7862-7868.
7. [3] For example, see M.A. Brook, C. Henry, R. Jueschke and P. Modi, Synlett, (1993) 97-104; C. Dallaire and M.A. Brook, Organometallics, 12 (1993) 2332-2338; H. Mayr and G. Gorath, J. Am. Chem. Soc., 117 (1995) 7862-7868.
8. [3] For example, see M.A. Brook, C. Henry, R. Jueschke and P. Modi, Synlett, (1993) 97-104; C. Dallaire and M.A. Brook, Organometallics, 12 (1993) 2332-2338; H. Mayr and G. Gorath, J. Am. Chem. Soc., 117 (1995) 7862-7868.
9. [4] For example, see A.G. Brook, G.L. LeGrow and D.M. MacRae, Can. J. Chem., 45 (1967) 239-253; P.F. Hudrlik and E.L.O. Agwaramgbo, in E.R. Corey, J.Y. Corey and P. Gaspar (eds.), Silicon Chemistry, Ellis Horwood, Chichester, 1988, pp. 95-104 and references cited therein.
10. [4] For example, see A.G. Brook, G.L. LeGrow and D.M. MacRae, Can. J. Chem., 45 (1967) 239-253; P.F. Hudrlik and E.L.O. Agwaramgbo, in E.R. Corey, J.Y. Corey and P. Gaspar (eds.), Silicon Chemistry, Ellis Horwood, Chichester, 1988, pp. 95-104 and references cited therein.
11. [5] G.L. Larson, V.C. de Maldonado, L.M. Fuentes and L.E. Torres, J. Org. Chem., 53 (1988) 633-639.
12. [6] K. Tamao and N. Ishida, Tetrahedron Lett., (1984) 4249-4252; I. Fleming and P.E.J. Sanderson, Tetrahedron Lett., 28 (1987) 4229-4232; S.S. Magar, R.C. Desai and P.L. Fuchs, J. Org. Chem., 57 (1992) 5360-5369; I. Fleming and S.B.D. Winter, Tetrahedron Lett., 34 (1993) 7287-7290; M.C. Norley, P.J. Kocienski and A. Faller, Synlett, (1994) 77-78; D.F. Taber, L. Yet and R.S. Bhamidipati, Tetrahedron Lett., 36 (1995) 351-354.
13. [6] K. Tamao and N. Ishida, Tetrahedron Lett., (1984) 4249-4252; I. Fleming and P.E.J. Sanderson, Tetrahedron Lett., 28 (1987) 4229-4232; S.S. Magar, R.C. Desai and P.L. Fuchs, J. Org. Chem., 57 (1992) 5360-5369; I. Fleming and S.B.D. Winter, Tetrahedron Lett., 34 (1993) 7287-7290; M.C. Norley, P.J. Kocienski and A. Faller, Synlett, (1994) 77-78; D.F. Taber, L. Yet and R.S. Bhamidipati, Tetrahedron Lett., 36 (1995) 351-354.
14. [6] K. Tamao and N. Ishida, Tetrahedron Lett., (1984) 4249-4252; I. Fleming and P.E.J. Sanderson, Tetrahedron Lett., 28 (1987) 4229-4232; S.S. Magar, R.C. Desai and P.L. Fuchs, J. Org. Chem., 57 (1992) 5360-5369; I. Fleming and S.B.D. Winter, Tetrahedron Lett., 34 (1993) 7287-7290; M.C. Norley, P.J. Kocienski and A. Faller, Synlett, (1994) 77-78; D.F. Taber, L. Yet and R.S. Bhamidipati, Tetrahedron Lett., 36 (1995) 351-354.
15. [6] K. Tamao and N. Ishida, Tetrahedron Lett., (1984) 4249-4252; I. Fleming and P.E.J. Sanderson, Tetrahedron Lett., 28 (1987) 4229-4232; S.S. Magar, R.C. Desai and P.L. Fuchs, J. Org. Chem., 57 (1992) 5360-5369; I. Fleming and S.B.D. Winter, Tetrahedron Lett., 34 (1993) 7287-7290; M.C. Norley, P.J. Kocienski and A. Faller, Synlett, (1994) 77-78; D.F. Taber, L. Yet and R.S. Bhamidipati, Tetrahedron Lett., 36 (1995) 351-354.
16. [6] K. Tamao and N. Ishida, Tetrahedron Lett., (1984) 4249-4252; I. Fleming and P.E.J. Sanderson, Tetrahedron Lett., 28 (1987) 4229-4232; S.S. Magar, R.C. Desai and P.L. Fuchs, J. Org. Chem., 57 (1992) 5360-5369; I. Fleming and S.B.D. Winter, Tetrahedron Lett., 34 (1993) 7287-7290; M.C. Norley, P.J. Kocienski and A. Faller, Synlett, (1994) 77-78; D.F. Taber, L. Yet and R.S. Bhamidipati, Tetrahedron Lett., 36 (1995) 351-354.
17. [6] K. Tamao and N. Ishida, Tetrahedron Lett., (1984) 4249-4252; I. Fleming and P.E.J. Sanderson, Tetrahedron Lett., 28 (1987) 4229-4232; S.S. Magar, R.C. Desai and P.L. Fuchs, J. Org. Chem., 57 (1992) 5360-5369; I. Fleming and S.B.D. Winter, Tetrahedron Lett., 34 (1993) 7287-7290; M.C. Norley, P.J. Kocienski and A. Faller, Synlett, (1994) 77-78; D.F. Taber, L. Yet and R.S. Bhamidipati, Tetrahedron Lett., 36 (1995) 351-354.
18. [7] For leading references, see (a) G. Fraenkel, R.E. Carter, A, McLachlan and J.H. Richards, J. Am. Chem. Soc., 82 (1960) 5846-5850;
19. (b) H. Spiesecke and W.G. Schneider, J. Chem. Phys., 35 (1961) 731-738;
20. (c) H. Spiesecke and W.G. Schneider, Tetrahedron Lett., (1961) 468-472;
21. (d) T.K. Wu and B.P. Dailey, J. Chem. Phys., 41 (1964) 2796-2806;
22. (e) J.B. Grutzner, J.M. Lawlor and L.M. Jackman, J. Am. Chem. Soc., 94 (1972) 2306-2315;
23. (f) G.L. Nelson, G.C. Levy and J.D. Cargioli, J. Am. Chem. Soc., 94 (1972) 3089-3094;
24. (g) G.J. Martin, M.L. Martin and S. Odiot, Org. Magn. Reson., 7 (1975) 2-17;
25. (h) D.H. O'Brien, A.J. Hart and C.R. Russell, J. Am. Chem. Soc., 97 (1975) 4410-4412;
26. (i) G.L. Nelson and E.A. Williams, Progr. Phys. Org. Chem., 12 (1976) 229-342;
27. (j) D.H. O'Brien, in E. Buncel and T. Durst (eds.), Comprehensive Carbanion Chemistry, Part A, Elsevier, Amsterdam, 1980, pp. 271-322;
28. (k) J.B. Grutzner, in J.B. Lambert and R. Rittner (eds.), Recent Advances in Organic NMR Spectroscopy, Norell Press, Landisville, NJ. 1987, pp. 17-42.
29. [8] E. Liepins, I. Zicmane and E. Lukevics, J. Organomet. Chem., 306 (1986) 167-182.
30. 13C NMR spectra of many additional phenylsilanes (as well as allyl, vinyl, and benzylsilanes) have been investigated: (a) P.E. Rakita, J.P. Srebro and L.S. Worsham, J. Organomet. Chem., 104 (1976) 27-37;
31. (b) P.E. Rakita, L.S. Worsham and J.P. Srebro, Org. Magn. Reson., 8 (1976) 310-316;
32. (c) P.E. Rakita and L.S. Worsham, J. Organomet. Chem., 137 (1977) 145-155;
33. (d) P.E. Rakita and L.S. Worsham, J. Organomet Chem. 139 (1977) 135-142.
34. [10] J. Schraml, R. Ponec, V. Chvalovsky, G. Engelhardt, H. Jancke, H. Kriegsmann, M.F. Larin, V.A. Pestunovich and M.G. Voronkov, J. Organomet. Chem., 178(1919) 55-73.
35. [11] J. Lipowitz, J. Am. Chem. Soc., 94 (1972) 1582-1589.
36. [12] (a) J.L. Speier, J. Am. Chem. Soc., 74 (1952) 1003-1010;
37. (b) S.H. Langer, S. Connell and I. Wender, J. Org. Chem., 23 (1958) 50-58;
38. (c) A. Marchand, J. Valade, M.-T. Forel, M.-L. Josien and R. Calas, J. Chim. Phys., 59 (1962) 1142-1150;
39. (d) G.G. Smith and C. Djerassi, Org. Mass Spectrom., 5 (1971) 487-489.
40. [13] (a) R.L. Scholl, G.E. Maciel and W.K. Musker, J. Am. Chem. Soc., 94 (1972) 6376-6385;
41. (b) M. Bordeau, J. Dédier, É. Frainnet, J.-P. Fayet and P. Mauret, J. Organomet. Chem., 59 (1973) 125-139; 61 (1973) 91-101;
42. (b) M. Bordeau, J. Dédier, É. Frainnet, J.-P. Fayet and P. Mauret, J. Organomet. Chem., 59 (1973) 125-139; 61 (1973) 91-101;
43. (c) L.B. Krivdin, G.A. Kalabin, R.G. Mirskov, N.K. Yarosh and M.G. Voronkov, Izu. Akad. Nauk SSSR, Ser. Khim., (1982) 2829-2832;
44. (d) É.É. Liepin'sh, I.A. Zitsmane, E. Lukevits, E.I. Dubinskaya and M.G. Voronkov, /. Gen. Chem. USSR, 53 (1983) 968-971.
45. [14] (a) J.W. Ryan, J. Am. Chem. Soc., 84 (1962) 4730-4734;
46. (b) Y. Iwakura, K. Uno, F. Toda, K. Hattori and M. Abe, Bull. Chem. Soc. Jpn., 44 (1971) 1400-1402;
47. (c) B. Bøe, J. Organomet. Chem., 57 (1973) 255-260;
48. (d) I. Ojima, T. Kogure, M. Nihonyanagi, H. Kono, S. Inaba and Y. Nagai, Chem. Lett., (1973) 501-504;
49. (e) P. Koehler, H. Geissler, M. Jakoubkova, G. Dube, K. Licht and H. Kriegsmann, Z. Anorg. Allg. Chem., 440 (1978) 183-196;
50. (f) T.C. Bedard and J.Y. Corey, J. Organomet. Chem., 428 (1992) 315-333;
51. (g) P.E. Dietze and Y. Xu, J. Org. Chem., 59 (1994) 5010-5016.
52. [15] H. Kelling, P. Schneider and G. Schott, Z. Anorg. Allg. Chem., 398 (1913) 301-311.
53. [16] (a) H. Oilman and G.N.R. Smart, J. Org. Chem., 19 (1954) 441-450;
54. (b) M. Takakusa, Bull. Chem. Soc. Jpn., 36 (1963) 284-287;
55. (c) R.L. Schowen and K.S. Latham, Jr., J. Am. Chem. Soc., 88 (1966) 3795-3797;
56. (d) J.-L. Bréfort, R.J.P. Corriu, C. Guérin, B.J.L. Henner and W.W.C. Wong Chi Man, Organometallics, 9 (1990) 2080-2085.
57. [17] (a) E. Åkerman, Acta Chem. Scand., 10 (1956) 298-305;
58. (b)E. Åkerman, Acta Chem. Scand., 11 (1957) 373-381;
59. (c) W.D. English and L.H. Sommer, Rev. Soc. Quim. Men., 6 (1962) 114-120;
60. (d) É. Frainnet and M. Paul, C.R. Acad. Sci., Paris, Ser. C, 265 (1967) 1185-1188.
61. [18] (a) J. Ancelle, G. Bertrand, M. Joanny and P. Mazerolles, Tetrahehedron Lett., (1979) 3153-3156;
62. (b) G. Bertrand, P. Mazerolles and J. Ancelle, Tetrahedron, 37 (1981) 2459-2466;
63. (c) S. Bain, S. Ijadi-Maghsoodi and T.J. Barton, Organometallics, 6 ( 1987) 1136-1138.
64. [19] (a) G.A. Kutyrev, R.T. Nigametzyanov, R.A. Cherkasov and A.N. Pudovik, J. Gen. Chem. USSR, 48 (1978) 690-694;
65. (b) J. Kowalski and J. Chojnowski, J. Organomet. Chem., 356 (1988) 285-295;
66. (c) Z.Y. Wei, D. Wang, J.S. Li and T.H. Chan, J. Org. Chem., 54 (1989) 5768-5774.
67. [20] (a) P. Voss, C. Meinicke, E. Popowski and H. Kelling, Z. Anorg. Allg. Chem., 439 (1978) 219-226;
68. (b) H. Kelling, P. Voss, R. Stendel and E. Popowski, Z. Anorg. Aug. Chem., 476 (1981) 55-61.
69. [21] (a) M.G. Voronkov, V.P. Freshin, L.S. Romanenko, J. Pola and V. Chvalovsky, Collect. Czech. Chem. Commun., 41 (1976) 2718-2723;
70. (b) R. Carleer and M.J.O. Anteunis, Org. Magn. Reson., 13 (1980) 253-258;
71. (c) J.J. Eisch and C.S. Chiu, Heteroat. Chem., 5 (1994) 265-274.
72. [22] (a) I. Ojima, S.-I. Inaba, T. Kogure, M. Matsumoto, H. Matsumoto, H. Watanabe and Y. Nagai, J. Organomet. Chem., 55 (1973) C4-C6;
73. (b) A.S. Gordetsov, I.A. Vostokov and Yu.I. Dergunov, J. Gen. Chem. USSR, 47 (1977) 345-349;
74. (c) P. Dubois Murphy, T. Taki, T. Sogabe, R. Metzler, T.G. Squires and B.C. Gerstein, J. Am. Chem. Soc., 101 (1979) 4055-4058;
75. (d) H. Watanabe, R. Akaba, T. Iezumi and Y. Nagai, Bull. Chem. Soc. Jpn., 53 (1980) 2981-2985.
76. [23] (a) K. Licht and H. Kriegsmann, Z. Anorg. Allg. Chem., 323 (1963) 190-206;
77. (b) J.F. Hampton, C.W. Lacefield and J.F. Hyde, Inorg. Chem., 4 (1965) 1659-1660;
78. (c) G.H. Barnes, Jr. and N.E. Daughenbaugh, J. Org. Chem., 31 (1966) 885-887.