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Synthesis 1988; 1988(2): 106-108
DOI: 10.1055/s-1988-27481
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Selective Formation of Alkyl Azides Using Trimethylsilyl Azide and Carbonyl Compounds

Kozaburo Nishiyama* , Tomoko Yamaguchi
  • *Department of Chemistry, Tokyo Metropolitan University, 2-1-1, Fukasawa, Setagaya, Tokyo 158, Japan
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Publication Date:
20 August 2002 (online)

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Whereas tin(II) chloride, or zinc chloride, catalyzed reaction of trimethylsilyl azide (TMSA) with carbonyl compounds gave gem-diazides 3, a catalytic amount of sodium azide/15-crown-5 promoted an addition reaction of TMSA toward these compounds to give α-siloxy azides 2 exclusively. A stereoelectronic effect was found to be important for these reactions.