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DOI: 10.1039/A901392J (Paper) Reference Section for: Chem. Commun., 1999, 893-894

Novel concise ring closure leading to bridged ten-membered ring compounds

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Hiroshi Fujishima, Hiroshi Takeshita, Masahiro Toyota and Masataka Ihara

Abstract

An unusual TBAF-mediated intramolecular cyclisation of diallylsilane derivatives 3 and 12 provided bicyclo[6.2.2]dodecanes 5 and 13 in good yields.

References

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  7. EtAlCl2, AlCl3, SnCl4 and TBDMSOTf were also investigated in these reactions, however, neither 4 nor 5 was obtained.
  8. Selected data for 5: δH(300 MHz, CDCl3) 1.17 (s, 3H), 1.35–1.59 (m, 4H), 1.84–1.99 (m, 2H), 2.90–3.01 (m, 1H), 3.11 (dt, J 4.8, 3.2, 1H), 3.79 (dd, J 8.8, 3.2, 1H), 5.25 (ddd, J 11.6, 9.2, 7.6, 1H), 5.31 (d, J 11.6 Hz), 5.71 (ddd, J 9.6, 5.2, 1.6 Hz), 5.81 (dd, J 9.6, 1.6 Hz), 5.83–5.92 (m, 2H); δC(75 MHz, CDCl3) 137.3, 137.2, 136.0, 128.7, 126.0, 123.8, 77.6, 44.5, 40.0, 31.1, 29.6, 25.9, 25.6.
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  11. Selected data for 13: δH(300 MHz, CDCl3): 0.79 (s, 3H), 0.93–0.99 (m, 4H), 1.21 (s, 3H), 1.40–1.60 (br s, 1H), 1.98 (dd, J 15.0, 8.8 Hz), 3.08–3.13 (m, 1H), 3.20 and 3.25 (each s, 2.8H and 0.2H), 3.99 (dd, J 8.8, 2.2 Hz), 4.67 (dd, J 9.2, 1.1 Hz), 5.09 (dd, J 12.5, 9.2 Hz), 5.52 (dd, J 12.5, 1.1 Hz), 5.70–5.90 (m, 4H); m/z 230 (M+– 18).
  12. Crystal data for 14: C16H22O2, plates, mp 34–35 °C, triclinic, P[1 with combining macron], a= 7.641(1), b= 15.890(3), c= 6.3477(9)Å, α= 96.66(1), β= 109.31(1), γ= 99.48(1)°, V= 705.3(2)Å3, Z= 2, µ= 0.75 cm–1, Dc= 1.169 g cm–3, F000 = 272, T= 150 K, R, Rw= 0.039, 0.038 for 2302 absorption–corrected reflections with I > 3.10 σ(I). CCDC 182/1220. see http://www.rsc.org/suppdata/cc/1999/893/ for crystallo-graphic files in .cif format.
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