Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 14
27
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Heteroannulation of Alkynyl Carbene Complexes: [3+2] Dipolar Cycloaddition of Pentacarbonyl-[(Alkynyl)(Methoxy)Carbene]Metals with Masked 1,3-Dipoles

, , , &
Pages 2043-2050 | Received 18 Apr 1994, Published online: 23 Sep 2006

References

  • Wulff , W. D. 1990 . Comprehensive Organic Synthesis , vol. 5 , p 1065 London : Pergamon Press .
  • Doetz , K. H. 1990 . New J. Chem. , 14 : 433
  • Anderson , B. A. , Bao , J. , Brandvold , T. A. , Challener , C. A. , Wulff , W. D. , Xu , Y.-C and Rheingold , A. L. 1993 . J. Am. Chem. Soc. , 115 : 10671
  • Meric , C. A. and Xu , D. 1991 . J. Am. Chem. Soc. , 113 : 7418
  • Doetz , K. H. and Deitz , R. 1978 . Chem. Ber. , 111 : 2517
  • Wulff , W. D. , McCallum , J. S. and Kunng , F.-A. 1988 . J. Am. Chem. Soc. , 110 : 7419 and references therein.
  • Chan , K. S. and Wulff , W. D. 1986 . J. Am. Chem. Soc. , 108 : 5229 At this point of time, only one related example of such reaction has been [3+2] dipolar cycloaddition of pentacarbonyl[(alkoxy)(alkynyl)-carbene]chromium with diazomethane, see:
  • Newton , C. G. and Ramsden , C. A. 1982 . Tetrahedron , 38 : 2965
  • Potts , K. T. 1984 . 1,3-Dipolar Cycloaddition Chemistry , vol. 2 , New York : Wiley .
  • Potts , K. T. , Baum , J. and Houghton , E. 1974 . J. Org. Chem. , 39 : 3631
  • McEwen , W. E. , Kanktkar , K. B. and Hung , W. M. 1971 . J. Am. Chem. Soc. , 93 : 4484 C-5 Atom of above both types of 1,3-dipoles attacks β-position of carbene complex owing to the delocalization of the exocyclic negative charge to the C-5 position of thiazole nucleus. For the regiochemistry of cycloaddition of these types of masked 1,3-dipoles. see:

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.