Synthesis and domino reactions of 1,1-bis(hydroxymethyl)allenes

(Note: The full text of this document is currently only available in the PDF Version )

Peter Langer


Abstract

The reaction of dilithiated 1,1-diphenylallene with aryl ketones provides a convenient access to novel 1,1-bis(hydroxymethyl)allenes, which undergo Friedel–Crafts-type domino reactions upon treatment with TsOH.


References

  1. For reviews of domino reactions, see: L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131 Search PubMed; A. de Meijere and F. E. Meyer, Angew. Chem., Int. Ed. Engl., 1994, 33, 2379 CrossRef.
  2. H. Hopf and G. Maas, Angew. Chem., Int. Ed. Engl., 1992, 31, 931 CrossRef; F. Toda, K. Tanaka, I. Sano and T. Isozaki, Angew. Chem., Int. Ed. Engl., 1994, 33, 1757 CrossRef; H. Hopf, P. G. Jones, P. Bubenitschek and C. Werner, Angew. Chem., Int. Ed. Engl., 1995, 34, 2367 CAS.
  3. S. Blechert, R. Knier, H. Schroers and T. Wirth, Synthesis, 1995, 592 CrossRef CAS; R. Grigg, V. Loganathan, V. Sridharan, P. Stevenson, S. Sukirthalingam and T. Worakun, Tetrahedron, 1996, 52, 11 479 CrossRef CAS; M. Schmittel, M. Strittmatter and S. Kiau, Angew. Chem., Int. Ed. Engl., 1996, 35, 1843 CrossRef CAS; T. Doi, A. Yanagisawa, S. Nakanishi, K. Yamamoto and T. Takahashi, J. Org. Chem., 1996, 61, 2602 CrossRef CAS; H. Nemoto, M. Yoshida and K. Fukumoto, J. Org. Chem., 1997, 62, 6450 CrossRef CAS.
  4. A 1,1-bis(hydroxymethyl)allene has been previously prepared by a different route in 17% yield: H. Mori, K. Ikoma and S. Katsumura, Chem. Commun., 1997, 2243 Search PubMed.
  5. P. Langer, M. Döring and D. Seyferth, Chem. Commun., 1998, 1927 RSC.
  6. S. Hagen, M. S. Bratcher, M. S. Erickson, G. Zimmermann and L. T. Scott, Angew. Chem., Int. Ed. Engl., 1997, 36, 406 CrossRef CAS.
  7. (a) F. Toda, N. Ooi and K. Akagi, Bull. Chem. Soc. Jpn., 1971, 44, 1050 CAS; (b) N. J. Head, G. A. Olah and G. K. S. Prakash, J. Am. Chem. Soc., 1995, 117, 11 205 CrossRef CAS.
  8. F. W. Nader and C.-D. Wacker, Angew. Chem., Int. Ed. Engl., 1985, 24, 851 CrossRef.
  9. For comparison, see: G. Dyker, F. Nerenz, P. Siemsen, P. Bubenitschek and P. G. Jones, Chem. Ber., 1996, 129, 1265 Search PubMed.
  10. M. Hoang, T. Gadosy, H. Ghazi, D.-F. Hou, A. C. Hopkinson, L. J. Johnston and E. Lee-Ruff, J. Org. Chem., 1998, 63, 7168 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.