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DOI: 10.1039/A802173B (Paper) Reference Section for: Chem. Commun., 1998, 1177-1178

One pot synthesis of mono- or bi-cyclic phosphiranes and phosphirenes

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Yannick Miquel, Alain Igau, Jean-Pierre Majoral, Maria Zablocka, Yannick Miquel and Aleksandra Skowronska

Abstract

Treatment of phospholene oxide 1, vinylphosphine oxide 11 or alkynylphosphine oxide 14 with [Cp2Zr] 2 followed by addition of a chlorophosphine leads to various phosphiranes and phosphirenes.

References

  1. F. Mathey, Chem. Rev., 1990, 90, 997 CrossRef CAS.
  2. N. Cénac, A. Chrostowska, J.-M. Sotiropoulos, B. Donnadieu, A. Igau, G. Pfister-Guillouzo and J.-P. Majoral, Organometallics, 1997, 16, 4551 CrossRef CAS; L. Dupuis, N. Pirio, P. Meunier, A. Igau, B. Donnadieu and J.-P. Majoral, Angew. Chem., Int. Ed. Engl., 1997, 36, 987 CrossRef CAS; M. Zablocka, A. Igau, B. Donnadieu, J.-P. Majoral and A. Skowronska, Chem. Commun., 1997, 1239 RSC and references cited therein.
  3. For recent reviews on zirconocene, see for example: Y. Hanzawa, H. Ito and T. Taguchi, Synlett, 1995, 299 Search PubMed; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov and U. Rosenthal, Synlett, 1996, 111 CrossRef CAS references cited therein.
  4. A dimeric form cannot be totally ruled out for 4, 12 and 15.
  5. M. Zablocka, A. Igau, J.-P. Majoral and K. M. Pietrusiewicz, Organometallics, 1993, 12, 603 CrossRef CAS.
  6. Selected data for 4: δC(CDCl3) 41.0 (d, JPC 96.0, PCHZr), 58.1 (d, JPC 13.5, CHZr), 33.2 (d, JPC 19.2, CH2), 29.0 (d, JPC 73.6, PCH2). For 5a: δC 26.3 [dd, JP(O)C 16.5, JPC 38.0, P(O)CHP], 24.7 (d, JPC 51.0, CHP), 24.3 [d, JPC 71.8, P(O)CH2], 22.5 (d, JPC 7.5, CH2). For 8: δC 21.6 (s, CH3), 22.4 (d, JPC 12.2, ZrCH2), 35.6 (s, ZrCHCH2), 39.4 (d, JPC 18.2, PCH2CH2), 40.0 (d, JPC 18.7, PCH2), 41.8 (d, JPC 3.3, ZrCH). For 13: δC 28.2 (dd, JPC 29.0, JPC= 13.0, CH), 25.5 (dd, JPC 13.5, JPC 2.9, CH2). For 15: δC 153.5 [d, 1JPC 59.7, P(O)CZr], 148.3 (d, JPC 6.1, ZrCPh). For 16a: δC 145.0 [dd, JPC 53.2, JP(O)C 10.2, P(O)C[double bond, length as m-dash]], 139.6 (dd, JPC 62.6, JP(O)C 2.7, PCPh).
  7. A. Mahieu, Y. Miquel, A. Igau, B. Donnadieu and J.-P. Majoral, Organometallics, 1997, 16, 3086 CrossRef CAS.
  8. Compound 9 was isolated as two isomers (PMe3/Et cis or trans)(refs. 11, 12). According to NMR spectroscopy only the trans isomer for 8 was formed. However, these data do not allow the determination of the position of the C[double bond, length as m-dash]C π-system in the phospholane ring with respect to the zirconacyclopropane fragment.
  9. Full desulfurisation occurs when 1 equiv. of 1b is treated with 2 equiv. of 2.
  10. See for example: M. Zablocka, F. Boutonnet, A. Igau, F. Dahan, J.-P. Majoral and K. M. Pietrusiewicz, Angew. Chem., Int. Ed. Engl., 1993, 32, 1735 Search PubMed; M. Zablocka, A. Igau, N. Cénac, B. Donnadieu, F. Dahan, J.-P. Majoral and K. M. Pietrusiewicz, J. Am. Chem. Soc., 1995, 117, 8083 CrossRef.
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