Synthesis and NMR spectroscopic characterization of Si-substituted 1-silacyclobutene derivatives

• Authors: Ezzat Khan , Bernd Wrackmeyer
• Languages of publication: EN

Abstracts

EN

Hydroboration of trialkyn-1-yl(organo)silanes with one equivalent and two equivalents of 9-borabicyclo[3.3.1]nonane, 9-BBN afford dialkyn-1-ylsilanes and alkyn-1-ylsilanes, respectively. The alkyn-1-ylsilane derivatives are stable at room temperature and can be store under dry argon for prolong period of time. These compounds are attractive materials for further rearrangements to afford novel 1-silacyclobutene derivatives bearing Si-alkenyl or Si-alkynyl functionalities. The hydroboration reaction is well controlled by the Si-R1 function, i.e., the starting silanes with R1 = Ph selectively afford hydroboration of one Si-C≡C bond with one equivalent of 9-BBN, leaving the other two functionalities untouched. Under mild reaction conditions (25°C), the starting silanes with R1 = Me lead to mixture containing dialkyn-1-ylsilane, alkyn-1-ylsilane and their respective 1-silacyclobutene derivatives. All new compounds are sensitive towards air and moisture and were studied by multinuclear magnetic resonance spectroscopy (1H, 13C, 11B, 29Si NMR) in solution.

Keywords

EN

Alkynyl(organo)silanes; Hydroboration; Vinylboration; Silacyclobutenes; NMR

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 1
• Pages: 126-132

Dates

published

1 - 2 - 2011

online

16 - 12 - 2010

Contributors

author

Ezzat Khan

author

Bernd Wrackmeyer

• Anorganische Chemie II, Universität Bayreuth, D-95440, Bayreuth, Germany

References

• [1] T. Takahashi, Z. Xi, Y. Obora, N. Suzuki, J. Am. Chem. Soc. 117, 2665 (1995) http://dx.doi.org/10.1021/ja00114a038[Crossref]
• [2] M. Horacek, N. Bazyakina, P. Stepnicka, R. Gyepes, I. Cisarova, S. Bredeau, P. Meunier, J. Kubista, K. Mach, J. Organomet. Chem. 628, 30 (2001) http://dx.doi.org/10.1016/S0022-328X(01)00746-X[Crossref]
• [3] A.C. Dema, C.M. Lukehart, A.T. McPhail, D.R. McPhail, J. Am. Chem. Soc. 112, 7229 (1990) http://dx.doi.org/10.1021/ja00176a023[Crossref]
• [4] J. Mohseni-Ala, N. Auner, Inorg. Chim. Acta 359, 4673 (2006) http://dx.doi.org/10.1016/j.ica.2006.10.001[Crossref]
• [5] K.C. Jin, V.T. Dang, Y. Ikee, T. Yamada, S. Sano, M. Shiro, Y. Nagao, Heterocycles 70, 71 (2006) http://dx.doi.org/10.3987/COM-06-S(W)14[Crossref]
• [6] N. Auner, C.R. Heikenwälder, C. Wagner, Organometallics 12, 4135 (1993) http://dx.doi.org/10.1021/om00034a056[Crossref]
• [7] G.T. Burns, T.J. Barton, J. Am. Chem. Soc. 105, 2006 (1983) http://dx.doi.org/10.1021/ja00345a056[Crossref]
• [8] B. Wrackmeyer, H.E. Maisel, E. Molla, A. Motalib, A. Badshah, M.H. Bhatti, S. Ali, Appl. Organomet. Chem. 17, 465 (2003) http://dx.doi.org/10.1002/aoc.460[Crossref]
• [9] B. Wrackmeyer, E. Khan, R. Kempe, Appl. Organomet. Chem. 21, 39 (2007) http://dx.doi.org/10.1002/aoc.1155[Crossref]
• [10] B. Wrackmeyer, E. Khan, S. Bayer, K. Shahid, Z. Naturforsch. 62b, 1174 (2007)
• [11] E. Khan, S. Bayer, B. Wrackmeyer, Z. Naturforsch. 64b, 47 (2009)
• [12] E. Khan, B. Wrackmeyer, Turk. J. Chem. (In press)
• [13] B. Wrackmeyer, E. Khan, R. Kempe, Appl. Organomet. Chem. 22, 383 (2008) http://dx.doi.org/10.1002/aoc.1411[Crossref]
• [14] W.E. Davidsohn, M.C. Henry, Chem. Rev. 67, 73 (1976) http://dx.doi.org/10.1021/cr60245a003[Crossref]
• [15] L. Brandsma, Preparative Acetylenic Chemistry, 2nd edition (Elsevier, Amsterdam, 1988)
• [16] L. Brandsma, Synthesis of Acetylenes, Allenes, Cumulenes - Methods and Techniques (Elsevier, Amsterdam, 2004)
• [17] B. Wrackmeyer, E. Khan, A. Badshah, E. Molla, P. Thoma, O.L. Tok, W. Milius, R. Kempe, J. Senker, Z. Naturforsch. 65b, 119 (2010)
• [18] B. Wrackmeyer, E. Khan, S. Bayer, O.L. Tok, E.V. Klimkina, W. Milius, R. Kempe, Z. Naturforsch. 65b, 725 (2010)
• [19] E. Khan, B. Wrackmeyer, R. Kempe, Eur. J. Inorg. Chem. 5367 (2008)
• [20] E. Khan, R. Kempe, B. Wrackmeyer, Appl. Organomet. Chem. 23, 204 (2009) http://dx.doi.org/10.1002/aoc.1497[Crossref]
• [21] G.A. Morris, R. Freeman, J. Am. Chem. Soc. 101, 760 (1979) http://dx.doi.org/10.1021/ja00497a058[Crossref]
• [22] G.A. Morris, J. Am. Chem. Soc. 102, 428 (1980) http://dx.doi.org/10.1021/ja00521a097[Crossref]
• [23] G.A. Morris, J. Magn. Reson. 41, 185 (1980)
• [24] D.P. Burum, R.R. Ernst, J. Magn. Reson. 39, 163 (1980)
• [25] B. Wrackmeyer, E. Khan, R. Kempe, Z. Anorg. Allg. Chem. 633, 453 (2007) http://dx.doi.org/10.1002/zaac.200600302[Crossref]
• [26] B. Wrackmeyer, H. E. Maisel, W. Milius, M.H. Bhatti, S. Ali, J. Organomet. Chem. 669, 72 (2003) http://dx.doi.org/10.1016/S0022-328X(02)02219-2[Crossref]
• [27] B. Wrackmeyer, E. Khan, W. Milius, Z. Naturforsch. 63b, 1267 (2008)
• [28] B. Wrackmeyer, E. Khan, R. Kempe, Z. Naturforsch. 62b, 75 (2007)
• [29] B. Wrackmeyer, Progr. NMR Spectrosc. 12, 227 (1979) http://dx.doi.org/10.1016/0079-6565(79)80003-5[Crossref]
• [30] B. Wrackmeyer, Annu. Rep. NMR Spectrosc. 20, 61 (1988) http://dx.doi.org/10.1016/S0066-4103(08)60170-2[Crossref]

Identifiers

DOI

10.2478/s11532-010-0122-z