All articles of this category 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.
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Nishiyama et al. (1988) studied this question.