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1
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Wiley-VCH, Weinheim, Germany
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Diederich F., Stang P.J., and Tykwinski R.R. Acetylene Chemistry (2004), Wiley-VCH, Weinheim, Germany
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(2004)
Acetylene Chemistry
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Diederich, F.1
Stang, P.J.2
Tykwinski, R.R.3
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7
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33748571531
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Zheng Q., Bohling J.C., Peters T.B., Frisch A.C., Hampel F., and Gladysz J.A. Chem. Eur. J. 12 (2006) 6486-6505
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Zheng, Q.1
Bohling, J.C.2
Peters, T.B.3
Frisch, A.C.4
Hampel, F.5
Gladysz, J.A.6
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11
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12344269243
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Luu T., Slepkov A.D., Eisler S., McDonald R., Hegmann F.A., and Tykwinski R.R. Org. Lett. 7 (2005) 51-54
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Org. Lett.
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Luu, T.1
Slepkov, A.D.2
Eisler, S.3
McDonald, R.4
Hegmann, F.A.5
Tykwinski, R.R.6
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12
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14744270102
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Eisler S., Slepkov A.D., Elliott E., Luu T., McDonald R., Hegmann F.A., and Tykwinski R.R. J. Am. Chem. Soc. 127 (2005) 2666-2676
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Eisler, S.1
Slepkov, A.D.2
Elliott, E.3
Luu, T.4
McDonald, R.5
Hegmann, F.A.6
Tykwinski, R.R.7
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14
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33646120606
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Rubin Y., Lin S.S., Knobler C.B., Anthony J., Boldi A.M., and Diederich F. J. Am. Chem. Soc. 113 (1991) 6943-6949
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Rubin, Y.1
Lin, S.S.2
Knobler, C.B.3
Anthony, J.4
Boldi, A.M.5
Diederich, F.6
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36
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33750044601
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We have recently used this reagent in a completely stereoselective synthesis (retention of configuration) of a (Z)-β-bromovinylsilane:
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We have recently used this reagent in a completely stereoselective synthesis (retention of configuration) of a (Z)-β-bromovinylsilane:. Williams I., Kariuki B.M., Reeves K., and Cox L.R. Org. Lett. 8 (2006) 4389-4392
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(2006)
Org. Lett.
, vol.8
, pp. 4389-4392
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Williams, I.1
Kariuki, B.M.2
Reeves, K.3
Cox, L.R.4
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37
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0001497199
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Examples of β-bromovinylsilanes in the literature are scarce:
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Examples of β-bromovinylsilanes in the literature are scarce:. Mitchell T.N., Wickenkamp R., Amamria A., Dicke R., and Schneider U. J. Org. Chem. 52 (1987) 4868-4874
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(1987)
J. Org. Chem.
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-
Mitchell, T.N.1
Wickenkamp, R.2
Amamria, A.3
Dicke, R.4
Schneider, U.5
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40
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0032516561
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-
Caporusso A.M., Barontini S., Pertici P., Vitulli G., and Salvadori P. J. Organomet. Chem. 564 (1998) 57-59
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(1998)
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Caporusso, A.M.1
Barontini, S.2
Pertici, P.3
Vitulli, G.4
Salvadori, P.5
-
42
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-
45049083442
-
-
note
-
2Na requires 493.0995.
-
-
-
-
43
-
-
33748672319
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-
For some recent examples of NBS-mediated bromodestannylation reactions proceeding with retention of configuration:
-
For some recent examples of NBS-mediated bromodestannylation reactions proceeding with retention of configuration:. Gracia J., and Thomas E.J. J. Chem. Soc., Perkin Trans. 1 (1998) 2865-2871
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(1998)
J. Chem. Soc., Perkin Trans. 1
, pp. 2865-2871
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Gracia, J.1
Thomas, E.J.2
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45
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0033578686
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Kittaka A., Asakura T., Kuze T., Tanaka H., Yamada N., Nakamura K.T., and Miyasaka T. J. Org. Chem. 64 (1999) 7081-7093
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(1999)
J. Org. Chem.
, vol.64
, pp. 7081-7093
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-
Kittaka, A.1
Asakura, T.2
Kuze, T.3
Tanaka, H.4
Yamada, N.5
Nakamura, K.T.6
Miyasaka, T.7
-
51
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-
0010150880
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-
2, which proceed with retention of configuration:
-
2, which proceed with retention of configuration:. Piers E., and Skerlj R.T. J. Org. Chem. 52 (1987) 4421-4423
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(1987)
J. Org. Chem.
, vol.52
, pp. 4421-4423
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Piers, E.1
Skerlj, R.T.2
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54
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-
0000838938
-
-
For other examples of β-iodovinylsilanes see:
-
For other examples of β-iodovinylsilanes see:. Hayami H., Sato M., Kanemoto S., Morizawa Y., Oshima K., and Nozaki H. J. Am. Chem. Soc. 105 (1983) 4491-4492
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(1983)
J. Am. Chem. Soc.
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Hayami, H.1
Sato, M.2
Kanemoto, S.3
Morizawa, Y.4
Oshima, K.5
Nozaki, H.6
-
59
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45049084106
-
-
note
-
Crystallographic data (excluding structure factors) for 10 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publications No. CCDC 686832. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or email: deposit@ccdc.cam.ac.uk).
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61
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33845963639
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For recent examples:
-
For recent examples:. Fuwa H., Ebine M., Bourdelais A.J., Baden D.G., and Sasaki M. J. Am. Chem. Soc. 128 (2006) 16989-16999
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 16989-16999
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-
Fuwa, H.1
Ebine, M.2
Bourdelais, A.J.3
Baden, D.G.4
Sasaki, M.5
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63
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2342598334
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Archibald S.C., Barden D.J., Bazin J.F.Y., Fleming I., Foster C.F., Mandal A.K., Mandal A.K., Parker D., Takaki K., Ware A.C., Williams A.R.B., and Zwicky A.B. Org. Biomol. Chem. 2 (2004) 1051-1064
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(2004)
Org. Biomol. Chem.
, vol.2
, pp. 1051-1064
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-
Archibald, S.C.1
Barden, D.J.2
Bazin, J.F.Y.3
Fleming, I.4
Foster, C.F.5
Mandal, A.K.6
Mandal, A.K.7
Parker, D.8
Takaki, K.9
Ware, A.C.10
Williams, A.R.B.11
Zwicky, A.B.12
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75
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37049071468
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-
Banks R.E., Mohialdin-Khaffaf S.N., Lal G.S., Sharif I., and Syvret R.G. J. Chem. Soc., Chem. Commun. (1992) 595-596
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(1992)
J. Chem. Soc., Chem. Commun.
, pp. 595-596
-
-
Banks, R.E.1
Mohialdin-Khaffaf, S.N.2
Lal, G.S.3
Sharif, I.4
Syvret, R.G.5
-
76
-
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0027324432
-
-
Matthews D.P., Miller S.C., Jarvi E.T., Sabol J.S., and McCarthy J.R. Tetrahedron Lett. 34 (1993) 3057-3060
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 3057-3060
-
-
Matthews, D.P.1
Miller, S.C.2
Jarvi, E.T.3
Sabol, J.S.4
McCarthy, J.R.5
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78
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-
0036315183
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-
Martin B., Possémé F., Le Barbier C., Carreaux F., Carboni B., Seiler N., Moulinoux J.-P., and Delcros J.-G. Bioorg. Med. Chem. 10 (2002) 2863-2871
-
(2002)
Bioorg. Med. Chem.
, vol.10
, pp. 2863-2871
-
-
Martin, B.1
Possémé, F.2
Le Barbier, C.3
Carreaux, F.4
Carboni, B.5
Seiler, N.6
Moulinoux, J.-P.7
Delcros, J.-G.8
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79
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33845298931
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Yu C.-S., Chiang L.-W., Wu C.-H., Hsu Z.-K., Lee M.-H., Pan S.-D., and Pei K. Synthesis (2006) 3835-3840
-
(2006)
Synthesis
, pp. 3835-3840
-
-
Yu, C.-S.1
Chiang, L.-W.2
Wu, C.-H.3
Hsu, Z.-K.4
Lee, M.-H.5
Pan, S.-D.6
Pei, K.7
-
80
-
-
45049084051
-
-
note
-
2Na requires 433.1795.
-
-
-
-
81
-
-
45049083812
-
-
note
-
107Ag requires 913.2478.
-
-
-
-
82
-
-
45049083536
-
-
note
-
Unmasking was only performed on phenyl end-capped masked hexayne 22 and not on TMS end-capped analogue 21. Under the conditions used to effect defluorosilylation, removal of the TMS end-caps in 21 would also occur to provide an extremely unstable free hexayne. Since the TMS protecting groups can be removed without inducing dehalosilylation, 21 represents a convenient monomer precursor for oligomerisation studies.
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