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Synlett 2010(15): 2361-2362  
DOI: 10.1055/s-0030-1258067
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Sodium Hydride

Abha Verma*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
e-Mail: averma2@uno.edu;
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Publication Date:
30 August 2010 (online)

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Sodium HydrideSynlett 2010; 2010(15): e8-e8
DOI: 10.1055/s-0030-1258558

Introduction

Sodium hydride (NaH) [¹] is an important reagent for the synthesis of both organic and inorganic compounds. It is used as a base for the deprotonation of alcohols, phenols, amides, ketones, esters, and stannanes, and thus it is widely used to promote condensations of carbonyl compounds via the Dieckmann, Stobbe, Darzens and Claisen condensations. Under aprotic conditions NaH is an effective reducing agent for disulfides, disilanes, azides, and isoquinolines.

NaH is produced by the direct reaction of hydrogen and liquid sodium. Pure NaH is colorless (mp 800 ˚C), although samples generally appear grey, and commercially available either as free-flowing grey powder (95% dry hydride) or as grey powder dispersed in mineral oil. Because of its rapid and irreversible reaction with water, NaH can be used to dry some organic solvents. NaH-based hydrogen storage systems are also being developed for use in fuel-cell vehicles.

As sodium hydride can behave both as a base and a source of hydride, this dual ability in the presence of an electrophile and suitable solvents results in the formation of selective products. [²] An interesting selectivity between NaH and potassium hydride was observed in the preparation of Macroviracin A where NaH yielded the desired macro­cyclic dilactone core. [²]

    References

  • 1a Mackay KM. Hydrogen Compounds of the Metallic Elements   Spon; London: 1966. 
    Google Scholar
  • 1b Hurd DT. An Introduction to the Chemistry of the Hydrides   Wiley; New York: 1952. 
    Google Scholar
  • 1c Wiberg E. Amberger E. Hydrides of the Elements of Main Groups I-IV   Elsevier; New York: 1971. 
    Google Scholar
  • 1d Hajos ZG. Duncan GR. Can. J. Chem.  1975,  53:  2971 
    Google Scholar
  • 1e Gawley RE. Hennings DD. In Encyclopedia of Reagents for Organic Synthesis   John Wiley & Sons Ltd.; Chichester: 2006. 
    Google Scholar
  • 1f DiPietro JP. Skolnik EG. Analysis of the Sodium Hydride-Based Hydrogen Storage System being developed by PowerBall Technologies LLC  US Department of Energy, Office of Power Technologies, 1999, 861-888
    Google Scholar
  • 2a Hesek D. Lee M. Noll BC. Fisher JF. Mobashery S. J. Org. Chem.  2009,  74:  2567 
    Google Scholar
  • 2b Takahashi S. Souma K. Hashimoto R. Koshino H. Nakata T. J. Org. Chem.  2004,  69:  4509 
    Google Scholar
  • 3 Kaur H. Izenwasser S. Verma A. Wade D. Stevens ED. Trudell ML. Bioorg. Med. Chem. Lett.  2009,  19:  6865 
    CrossrefGoogle Scholar
  • 4 Garud DR. Toyoda Y. Koketsu M. Tetrahedron Lett.  2009,  50:  3035 
    CrossrefGoogle Scholar
  • 5 Oukli N. Comesse S. Chafi N. Oulyadi H. Daïch A. Tetrahedron Lett.  2009,  50:  1459 
    CrossrefGoogle Scholar
  • 6 Rountree JSS. Murphy PV. Org. Lett.  2009,  11:  871 
    CrossrefGoogle Scholar
  • 7 Yadav LDS. Srivastava VP. Patel R. Tetrahedron Lett.  2008,  49:  5652 
    Google Scholar
  • 8 Nagase H. Yamamoto N. Nemoto T. Yoza K. Kamiya K. Hirono S. Momen S. Izumimoto N. Hasebe K. Mochizuki H. Fujii H. J. Org. Chem.  2008,  73:  8093 
    CrossrefGoogle Scholar
  • 9 Yadav LDS. Rai A. Rai VK. Awasthi C. Tetrahedron Lett.  2008,  49:  687 
    CrossrefGoogle Scholar