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
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH14712
RESEARCH ARTICLE
Contents Vol 68(5)

Diethylaluminium Azide: A Versatile Reagent in Organic Synthesis

Serena Monticelli A and Vittorio Pace A B
+ Author Affiliations
- Author Affiliations

A Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 A-1090 Vienna, Austria.

B Corresponding author. Email: vittorio.pace@univie.ac.at

Australian Journal of Chemistry 68(5) 703-706 https://doi.org/10.1071/CH14712
Submitted: 15 December 2014  Accepted: 27 January 2015   Published: 2 April 2015

Abstract

The unique properties of diethylaluminium azide – arising from the Lewis acid aluminium and the nucleophilicity of the azide – make it a versatile reagent in organic synthesis. Ring-opening of epoxides, Michael-type additions, synthesis of acyl azides, and functionalizations of fullerene C60 will be discussed. Among the recently described uses of the reagent, particular attention will be devoted to the powerful Sedelmeier’s method to access 1H-tetrazol starting from nitriles.


References

[1]  K. Dehnicke, J. Strähle, D. Seybold, J. Müller, J. Organomet. Chem. 1966, 6, 298.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF28Xkslelsrw%3D&md5=b9dd9e6d0eabd44788d520a7ee1a3772CAS |

[2]  M. I. Prince, K. Weiss, J. Organomet. Chem. 1966, 5, 584.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF28Xkt12msL8%3D&md5=d1ae3609928e9f8d7bc75647c149582aCAS |

[3]  S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. Int. Ed. 2005, 44, 5188.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  H. Babu Mereyala, B. Frei, Helv. Chim. Acta 1986, 69, 415.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  F. Benedetti, F. Berti, S. Norbedo, Tetrahedron Lett. 1998, 39, 7971.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmvVShurY%3D&md5=f321b2b2ae1cb82a1939047493cad240CAS |

[6]  C. E. Davis, J. L. Bailey, J. W. Lockner, R. M. Coates, J. Org. Chem. 2003, 68, 75.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XovFSku7g%3D&md5=6c2a857f98e5ecda32cc65285194a1e5CAS | 12515464PubMed |

[7]  W. Nagata, M. Yoshioka, T. Terasawa, J. Am. Chem. Soc. 1972, 94, 4672.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38XkslGgtLg%3D&md5=867c2bc5d57acd902dc418e559fca03eCAS |

[8]  B. Y. Chung, Y. S. Park, I. S. Cho, B. C. Hyun, Bull. Korean Chem. Soc. 1988, 9, 269.
         | 1:CAS:528:DyaL1MXhtFCgs7Y%3D&md5=6d05c051257ffb179556c7e9cec8592eCAS |

[9]  I. Adamo, F. Benedetti, F. Berti, G. Nardin, S. Norbedo, Tetrahedron Lett. 2003, 44, 9095.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXovF2ltrc%3D&md5=2b892cc53efd15d4a3124c6cf60a089bCAS |

[10]  V. H. Rawal, H. M. Zhong, Tetrahedron Lett. 1994, 35, 4947.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXltleltr8%3D&md5=ad0d2e2a1fe5be2ff05730d3946a5b59CAS |

[11]  V. Aureggi, G. Sedelmeier, Angew. Chem. Int. Ed. 2007, 46, 8440.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlOks7%2FF&md5=4f475e31e5090105f38a4e2669f00d26CAS |

[12]  J. Roh, K. Vávrová, A. Hrabálek, Eur. J. Org. Chem. 2012, 6101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFGhtLbN&md5=038e5dcae69743bfdc287a87e0427a15CAS |

[13]  A. R. Akhmetov, I. R. Yarullin, A. R. Tuktarov, U. M. Dzhemilev, Tetrahedron Lett. 2014, 55, 3747.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXpslyqsLY%3D&md5=04b43c2eea5385d54a7ea82dd29bf67dCAS |