Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

1,2-Disilabicyclo[1.1.1]pentan-4-ones from a Disilenide and Acryloyl Chlorides

Andreas Rammo A , Iulia Bejan A , Antje Meltzer A , Krzysztof Radacki B , Holger Braunschweig B and David Scheschkewitz A C
+ Author Affiliations
- Author Affiliations

A Saarland University, Krupp-Chair for General and Inorganic Chemistry, Campus Dudweiler, Am Markt, Zeile 1, 66125 Saarbrücken-Dudweiler, Germany.

B Julius-Maximilian-University, Institute of Inorganic Chemistry, Am Hubland, 97074 Würzburg, Germany.

C Corresponding author. Email: scheschkewitz@mx.uni-saarland.de

Australian Journal of Chemistry 66(10) 1311-1314 https://doi.org/10.1071/CH13265
Submitted: 23 May 2013  Accepted: 19 June 2013   Published: 25 July 2013

Abstract

Reactions of a disilenide, a disila analogue of vinyl lithiums, with two α,β-unsaturated carboxylic acid chlorides yield the first examples of compounds with a bicyclo[1.1.1]pentane scaffold that feature one carbon and one silicon atom at bridgehead positions; the formation of 1,2-disilabicyclo[1.1.1]pentan-4-ones is explained with initial nucleophilic substitution at the carbonyl C-atom by the nucleophilic disilenide and subsequent intramolecular [2+2]-cycloaddition of the Si=Si to the C=C double bond in a highly diastereoselective fashion.


References

[1]  R. West, M. J. Fink, J. Michl, Science 1981, 214, 1343.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XhtVCgt74%3D&md5=7f505a6d042fe04a7eabd83ae633609fCAS | 17812259PubMed |

[2]  (a) R. Okazaki, R. West, Adv. Organomet. Chem. 1996, 39, 231.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XivVektrg%3D&md5=4c9baa692318393d2d0d3fed8f43f604CAS |
      (b) P. P. Power, Chem. Rev. 1999, 99, 3463.
         | Crossref | GoogleScholarGoogle Scholar |
         (c) M. Weidenbruch, in The Chemistry of Organic Silicon Compounds (Eds Z. Rappoport, Y. Apeloig) 2001, Vol. 3, Ch. 5, pp. 391–428 (Wiley: Chichester).
         (d) M. Karni, Y. Apeloig, J. Kapp, P. von R. Schleyer, in The Chemistry of Organic Silicon Compounds (Eds Z. Rappoport, Y. Apeloig) 2001, Vol. 3, Ch. 1, pp. 1–163 (Wiley: Chichester).
      (e) M. Kira, T. Iwamoto, Adv. Organomet. Chem. 2006, 54, 73.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. Scheschkewitz, Chem. – Eur. J. 2009, 15, 2476.
         | Crossref | GoogleScholarGoogle Scholar |
         (g) V. Ya. Lee, A. Sekiguchi, Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb: From Phantom Species to Stable Compounds 2010, Ch. 5 (Wiley: Chichester).
      (h) D. Scheschkewitz, Chem. Lett. 2011, 40, 2.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  D. Scheschkewitz, Angew. Chem. Int. Ed. 2004, 43, 2965.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXksl2qtr0%3D&md5=f515be8f7ea40d687287407b6ba65914CAS |

[4]  (a) M. Ichinohe, K. Sanuki, S. Inoue, Organometallics 2004, 23, 3088.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXktVKmt7w%3D&md5=d27ab0a3f25f74c8a6ae4f98e4bec28bCAS |
      (b) S. Inoue, M. Ichinohe, A. Sekiguchi, Chem. Lett. 2005, 34, 1564.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. Kinjo, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 2007, 129, 26.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) T.-l. Nguyen, D. Scheschkewitz, J. Am. Chem. Soc. 2005, 127, 10174.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. Abersfelder, D. Güclü, D. Scheschkewitz, Angew. Chem. Int. Ed. 2006, 45, 1643.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) M. J. Cowley, K. Abersfelder, A. J. P. White, M. Majumdar, D. Scheschkewitz, Chem. Commun. 2012, 48, 6595.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) T. Iwamoto, M. Kobayashi, K. Uchiyama, S. Sasaki, S. Nagendran, H. Isobe, M. Kira, J. Am. Chem. Soc. 2009, 131, 3156.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) M. Ichinohe, K. Sanuki, S. Inoue, A. Sekiguchi, Silicon Chem. 2007, 3, 111.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) S. Inoue, M. Ichinohe, A. Sekiguchi, Angew. Chem. 2007, 119, 3410.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) S. Inoue, M. Ichinohe, A. Sekiguchi, Angew. Chem. Int. Ed. 2007, 46, 3346.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) I. Bejan, D. Scheschkewitz, Angew. Chem. Int. Ed. 2007, 46, 5783.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Jeck, I. Bejan, A. J. P. White, D. Nied, F. Breher, D. Scheschkewitz, J. Am. Chem. Soc. 2010, 132, 17306.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. Abersfelder, T.-l. Nguyen, D. Scheschkewitz, Z. Anorg. Allg. Chem. 2009, 635, 2093.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) M. Hartmann, A. Haji-Abdi, K. Abersfelder, P. R. Haycock, A. J. P. White, D. Scheschkewitz, Dalton Trans. 2010, 39, 9288.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) K. Abersfelder, D. Scheschkewitz, J. Am. Chem. Soc. 2008, 130, 4114.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) D. Scheschkewitz, Angew. Chem. Int. Ed. 2005, 44, 2954.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) K. Abersfelder, A. J. P. White, H. S. Rzepa, D. Scheschkewitz, Science 2010, 327, 564.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) K. Abersfelder, A. J. P. White, R. J. F. Berger, H. S. Rzepa, D. Scheschkewitz, Angew. Chem. Int. Ed. 2011, 50, 7936.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) S. Inoue, M. Ichinohe, A. Sekiguchi, Chem. Lett. 2008, 37, 1044.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) I. Bejan, D. Güclü, S. Inoue, M. Ichinohe, A. Sekiguchi, D. Scheschkewitz, Angew. Chem. Int. Ed. 2007, 46, 3349.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlsVKgtr4%3D&md5=1a5d99fb70de7a8a44499056c860e154CAS |
      (b) P. R. Jones, T. F. O. Lim, J. Am. Chem. Soc. 1977, 99, 2013.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) N. Wiberg, G. Wagner, Angew. Chem. Int. Ed. 1983, 22, 1005.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) N. Auner, Z. Anorg. Allg. Chem. 1988, 558, 87.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) G. Delpon-Lacaze, C. Couret, J. Organomet. Chem. 1994, 480, c14.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) M. Mickoleit, R. Kempe, H. Oehme, Chem. – Eur. J. 2001, 7, 987.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) I. Bejan, S. Inoue, M. Ichinohe, A. Sekiguchi, D. Scheschkewitz, Chem. – Eur. J. 2008, 14, 7119.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVKhtr7L&md5=3e68b95599cc43f5f40ba6a00b07564eCAS | 18626876PubMed |
      (b) Y. Apeloig, M. Bendikov, M. Yuzefoviv, M. Nakash, D. Bravo-Zhivotovskii, D. Bläser, R. Boese, J. Am. Chem. Soc. 1996, 118, 12228.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) K. Sakamoto, J. Ogasawara, Y. Kon, T. Sunagawa, C. Kabuto, M. Kira, Angew. Chem. Int. Ed. 2002, 41, 1402.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) S. Inoue, M. Ichinohe, A. Sekiguchi, Angew. Chem. Int. Ed. 2007, 46, 3346.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Igarashi, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 2007, 129, 12660.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  M. B. Sponsler, D. A. Dougherty, J. Org. Chem. 1984, 49, 4978.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXltlKg&md5=e3f4b752e7ad76fddff9365f32401900CAS |

[9]  (a) J. A. Hardwick, K. M. Baines, Organometallics 2010, 29, 1305.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhs1Gmt74%3D&md5=08a9e1bd1794a2f2b5fef73deb246bf2CAS |
      (b) S. E. Gottschling, M. C. Jennings, K. M. Baines, Can. J. Chem. 2005, 83, 1568.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. E. Gottschling, K. K. Milnes, M. C. Jennings, K. M. Baines, Organometallics 2005, 24, 3811.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) M. S. Samuel, H. A. Jenkins, D. W. Hughes, K. M. Baines, Organometallics 2003, 22, 1603.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) C. E. Dixon, D. W. Hughes, K. M. Baines, J. Am. Chem. Soc. 1998, 120, 11049.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  R. Srinivasan, K. H. Carlough, J. Am. Chem. Soc. 1967, 89, 4932.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2sXkvF2gtbY%3D&md5=0746748210baa6b05e8c311b32eaaa34CAS |

[11]  T. Iwamoto, D. Tsushima, E. Kwon, S. Ishida, H. Isobe, Angew. Chem. Int. Ed. 2012, 51, 2340.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsF2lu77P&md5=e03f43e152e93c0058f5d210ee5ec027CAS |

[12]  Y. Kabe, T. Kawase, J. Okada, O. Yamashita, M. Goto, S. Masamune, Angew. Chem. Int. Ed. 1990, 29, 794.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  P. C. Bulman Page, S. S. Klair, S. Rosenthal, Chem. Soc. Rev. 1990, 19, 147.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  (a) N. Nakata, T. Oikawa, T. Matsumoto, Y. Kabe, A. Sekiguchi, Organometallics 2005, 24, 3368.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXkvVGktL8%3D&md5=b2fad8edf4c749518e36c631984e39b7CAS |
      (b) K. Narasaka, N. Saio, Y. Hayashi, H. Ichida, Chem. Lett. 1990, 19, 1411.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  G. Sheldrick, Acta Crystallogr. 2008, A64, 112.