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2012 | 10 | 5 | 1633-1639
Tytuł artykułu

Synthesis, NMR characterization and reactivity of 1-silacyclohex-2-ene derivatives

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The chloro functionality of allyldichlorosilane (HSiCl2(C3H5)) and allyldichloromethylsilane (MeSiCl2(C3H5)) were replaced by alkynyl groups and new compounds, allyldialkynylsilane 1 and allyldialkynylmethylsilane 2, were obtained. These silanes, which served as starting materials for the onward reactions, were purified by fractional distillation. They were further subjected to hydroboration with 9-BBN (9-borabicyclo[3.3.1]nonane) and were converted into 1-silacyclohex-2-ene derivatives 5 and 6. The competition between C≡C and C=C in the reaction was studied. The hydroborating reagent 9-BBN was expected to prefer terminal C=C bonds and to leave C≡C bond untouched. This hypothesis of preferable hydroboration was experimentally proved, and hence, 1-silacyclohex-2-ene derivatives were obtained in reasonably pure form. The reaction of allyldialkynylsilane 2 with one equivalent of 9-BBN affords 1-silacyclohex-2-ene bearing Si-C≡C-function, ready to be hydroborated further with one equivalent of 9-BBN. The obtained compound bears two C-B bonds, which are attractive synthones for further transformations. This study aims to highlight the chemistry of C-B and Si-H functional groups. All new compounds obtained were colorless air and moisture sensitive oils, and they were studied by multinuclear magnetic resonance spectroscopy (1H, 13C, 11B, 29Si NMR) in solution. [...]
Wydawca

Czasopismo
Rocznik
Tom
10
Numer
5
Strony
1633-1639
Opis fizyczny
Daty
wydano
2012-10-01
online
2012-07-21
Twórcy
autor
  • Department of Chemistry, University of Malakand, Chakdara, Dir(Lower), Khyber Pakhtunkhwa, 18550, Pakistan, ekhan@uom.edu.pk
  • Inorganic Chemistry II, University of Bayreuth, D-95440, Bayreuth, Germany
Bibliografia
  • [1] W.Y. Wong, C.K. Wong, G.L. Lu, K.W. Cheah, J.X. Shi, Z. Lin, J. Chem. Soc., Dalton Trans. 24, 4587 (2002) http://dx.doi.org/10.1039/b207575j[Crossref]
  • [2] M.A. Bennett, C.J. Cobley, D.C.R. Hockless, T. Klettke, Aust. J. Chem. 52(1), 51 (1999) http://dx.doi.org/10.1071/C98135[Crossref]
  • [3] A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. Burkalov, U. Rosenthal, Synlett 1996(2), 111 (1996) http://dx.doi.org/10.1055/s-1996-5338[Crossref]
  • [4] C.S. Griffith, G.A. Koutsantonis, B.W. Skelton, A.H. White, Angew. Chem. Int. Ed. 44(20), 3038 (2005) http://dx.doi.org/10.1002/anie.200500224[Crossref]
  • [5] U. Rosenthal, V.V. Burlakov, P. Arndt, W. Baumann, A. Spannenberg, Organometallics 22(5), 884 (2003) http://dx.doi.org/10.1021/om0208570[Crossref]
  • [6] Q. Zhou, X. Feng, L. Ni, J. Chen, J. Appl. Polym. Sci. 102(3), 2488 (2006) http://dx.doi.org/10.1002/app.24605[Crossref]
  • [7] D.B. Wiley, G. Kaplan, T. Dobbins, US Patent Application No. PCT/US2002/027126 (2003)
  • [8] D.B. Wiley, G. Kaplan, T. Dobbins, US Patent Application No. 20050076560 (2005)
  • [9] W.Y. Wong, C.K. Wong, G.L. Lu, A.W.M. Lee, K.W. Cheah, J.X. Shi, Macromolecules 36(4), 983 (2003) http://dx.doi.org/10.1021/ma021209v[Crossref]
  • [10] W.Y. Wong, C.K. Wong, G.L. Lu, J. Organomet. Chem. 671(1–2), 27 (2003) http://dx.doi.org/10.1016/S0022-328X(03)00003-2[Crossref]
  • [11] W.Y. Wong, A.W.M. Lee, C.K. Wong, G.L. Lu, H. Zhang, T. Mo, K.T. Lam, New J. Chem. 26(3), 354 (2002) http://dx.doi.org/10.1039/b108510g[Crossref]
  • [12] Q. Zhou, X. Feng, L. Ni, J. Chen, J. Appl. Polym. Sci. 102(3), 2488 (2006) http://dx.doi.org/10.1002/app.24605[Crossref]
  • [13] H.C. Brown, Organic Synthesis via Boranes (John Wiley and Sons, New York, 1975)
  • [14] H.C. Brown, Tetrahedron 12, 117 (1961) http://dx.doi.org/10.1016/0040-4020(61)80107-5[Crossref]
  • [15] H.C. Brown, S.U. Kulkarni, J. Organomet. Chem. 218, 299 (1981) http://dx.doi.org/10.1016/S0022-328X(00)81001-3[Crossref]
  • [16] H.C. Brown, M. Zaidlewicz, Organic syntheses via boranes. Vol. 2, Recent developments (Wis. Aldrich Chemical, Milwaukee, 2001)
  • [17] E.F. Knight, H.C. Brown, J. Am. Chem. Soc. 90(19), 5281 (1968) http://dx.doi.org/10.1021/ja01021a047[Crossref]
  • [18] R. Köster, G. Seidel, F. Lutz, C. Krüger, G. Kehr, B. Wrackmeyer, Chem. Ber. 127(5), 813 (1994) http://dx.doi.org/10.1002/cber.19941270504[Crossref]
  • [19] B. Wrackmeyer, Coord. Chem. Rev. 145, 125 (2005)
  • [20] B. Wrackmeyer, E. Khan, R. Kempe, Appl. Organomet. Chem. 21, 39 (2007) http://dx.doi.org/10.1002/aoc.1155[Crossref]
  • [21] B. Wrackmeyer, E. Khan, S. Bayer, K. Shahid, Z. Naturforsch. 62b, 1174 (2007)
  • [22] B. Wrackmeyer, E. Khan, R. Kempe, Appl. Organomet. Chem. 22, 383 (2008) http://dx.doi.org/10.1002/aoc.1411[Crossref]
  • [23] E. Khan, B. Wrackmeyer, R. Kempe, Eur. J. Inorg. Chem. 5367 (2008)
  • [24] E. Khan, R. Kempe, B. Wrackmeyer, Appl. Organomet. Chem. 23, 204 (2009) http://dx.doi.org/10.1002/aoc.1497[Crossref]
  • [25] E. Khan, B. Wrackmeyer, Cent. Eur. J. Chem. 9, 126 (2011) http://dx.doi.org/10.2478/s11532-010-0122-z[Crossref]
  • [26] E. Khan, B. Wrackmeyer, Turk. J. Chem. 34, 793 (2010)
  • [27] J. Mohseni-Ala, N. Auner, Inorg. Chim. Acta, 359, 4677 (2006) http://dx.doi.org/10.1016/j.ica.2006.05.024[Crossref]
  • [28] W. Uhl, D. Heller, J. Köster, E. Würthwein, N. Ghavtadze, Eur. J. Inorg. Chem. 1359 (2012).
  • [29] J.D. Sellars, P.G. Steel, M.J. Turner, Chem. Commun. 2385 (2006) [Crossref]
  • [30] J.D. Sellars, P.G. Steel, Org. Biomol. Chem. 4, 3223 (2006) http://dx.doi.org/10.1039/b608989e[Crossref]
  • [31] N.J. Hughes, R.D. C. Pullin, M.J. Sanganee, J.D. Sellars, P.G. Steel, M.J. Turner, Org. Biomol. Chem. 5, 2841 (2007) http://dx.doi.org/10.1039/b709318g[Crossref]
  • [32] A. Naka, S. Ueda, J. Ohshita, A. Kunai, T. Miura, H. Kobayashi, M. Ishikawa, Organometallics, 27(13), 2922 (2008) http://dx.doi.org/10.1021/om800219n[Crossref]
  • [33] B. Wrackmeyer, O.L. Tok, R. Kempe, Inorg. Chim. Acta 358, 4183 (2005) http://dx.doi.org/10.1016/j.ica.2005.03.016[Crossref]
  • [34] B. Wrackmeyer, O.L. Tok, W. Milius, A. Khan, A. Badshah, Appl. Organomet. Chem. 20(1), 99 (2006) http://dx.doi.org/10.1002/aoc.1020[Crossref]
  • [35] B. Wrackmeyer, O.L. Tok, Y.N. Bobnov, Angew. Chem. 111, 214 (1999) http://dx.doi.org/10.1002/(SICI)1521-3757(19990115)111:1/2<214::AID-ANGE214>3.0.CO;2-6[Crossref]
  • [36] B. Wrackmeyer, O.L. Tok, Y.N. Bobnov, Angew. Chem. Int. Ed. 38, 124 (1999) http://dx.doi.org/10.1002/(SICI)1521-3773(19990115)38:1/2<124::AID-ANIE124>3.0.CO;2-1[Crossref]
  • [37] B. Wrackmeyer, O.L. Tok, Y.N. Bobnov, Appl. Organomet. Chem. 18, 43 (2004) http://dx.doi.org/10.1002/aoc.555[Crossref]
  • [38] B. Wrackmeyer, E. Khan, R. Kempe, Z. Naturforsch. 62b, 75 (2007)
  • [39] B. Wrackmeyer, M. Milius, M.H. Bhatti, S. Ali, J. Organomet. Chem. 669, 72 (2003) http://dx.doi.org/10.1016/S0022-328X(02)02219-2[Crossref]
  • [40] B. Wrackmeyer, E. Khan, W. Milius, Z. Naturforsch. 63b, 1267 (2008).
  • [41] B. Wrackmeyer, E. Khan, S. Bayer, O.L. Tok, E.V. Klimkina, W. Milius, R. Kempe, Z. Naturforsch. 65b, 725 (2010)
  • [42] B. Wrackmeyer, E. Khan, A. Badshah, E. Molla, P. Thoma, O.L. Tok, W. Milius, R. Kempe, J. Senker, Z. Naturforsch. 65b, 119 (2010)
  • [43] W.E. Davidsohn, M.C. Henry, Chem. Rev. 67, 73 (1976) http://dx.doi.org/10.1021/cr60245a003[Crossref]
  • [44] L. Brandsma, Preparative Acetylenic Chemistry, 2nd edition (Elsevier, Amsterdam, 1988)
  • [45] L. Brandsma, L. Synthesis of Acetylenes, Allenes, Cumulenes-Methods and Techniques (Elsevier, Amsterdam, 2004)
  • [46] G.A. Morris, R. Freeman, J. Am. Chem. Soc.101, 760 (1979) http://dx.doi.org/10.1021/ja00497a058[Crossref]
  • [47] G.A. Morris, J. Am. Chem. Soc. 102, 428 (1980) http://dx.doi.org/10.1021/ja00521a097[Crossref]
  • [48] G.A. Morris, J. Magn. Reson. 41, 185 (1980)
  • [49] D.P. Burum, R.R. Ernst, J. Magn. Reson. 39, 163 (1980)
  • [50] J.M. Mallan, R.L. Bebb, Chem. Rev. 69, 693 (1969) http://dx.doi.org/10.1021/cr60261a006[Crossref]
  • [51] M. Braun, Angew. Chem. Int. Ed. 37, 430 (1998) http://dx.doi.org/10.1002/(SICI)1521-3773(19980302)37:4<430::AID-ANIE430>3.0.CO;2-5[Crossref]
  • [52] B. Wrackmeyer, E. Khan, R. Kempe, Z. Naturforsch. 63b, 275 (2008)
  • [53] R.S. Dhillon, Hydroboration and organic synthesis 9-borabicyclo[3.3.1]nonane 9-BBN (Springer-Verlag, Berlin, Heidelberg, 2007)
  • [54] H.C. Brown, A.W. Moerikofer, J. Am. Chem. Soc. 85, 2063 (1963) http://dx.doi.org/10.1021/ja00897a008[Crossref]
  • [55] C.A. Brown, R.A. Coleman, J. Org. Chem. 44, 2328 (1979) http://dx.doi.org/10.1021/jo01327a079[Crossref]
  • [56] E. Khan, R. Kempe, B. Wrackmeyer, Appl. Organomet. Chem. 23, 124 (2009) http://dx.doi.org/10.1002/aoc.1482[Crossref]
  • [57] B. Wrackmeyer, Prog. Nucl. Magn. Reson. Spectrosc. 12, 227 (1979) http://dx.doi.org/10.1016/0079-6565(79)80003-5[Crossref]
  • [58] A. Pelter, K. Smith, H.C. Brown, Borane Reagents (Academic Press, London, 1988)
  • [59] R. Köster, In: R. Köster (Ed.), Houben-Weyl, Methoden der Organischen Chemie (Thieme verlag, Stuttgart, 1984) Vol. 13/3c, 215–376
  • [60] E. Khan, S. Bayer, R. Kempe, B. Wrackmeyer, Eur. J. Inorg. Chem. 4416 (2009)
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0079-1
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