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ChemInform Abstract: The Reaction of Nitramines and Their N-Trimethylsilyl Derivatives with N,N-Bis(trimethylsilyloxy)enamines.

✍ Scribed by S. L. IOFFE; L. M. MAKARENKOVA; YU. A. STRELENKO; I. V. BLIZNETS; V. A. TARTAKOVSKY

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

The Reaction of Nitramines and Their N-Trimethylsilyl Derivatives with N,N-Bis(trimethylsilyloxy)enamines.

-Trimethylsilylated alkylnitramine (I) reacts with N,N-bis(trimethylsilyloxy)aminopropene (II) as N-centered nucleophile to afford selectively the trimethylsilylated oxime (III) which on hydrolysis provides access to hitherto unknown Ξ±-(Nnitro)alkylaminoacetone oxime (IV). In contrast, the non-silylated nitramine (V) reacts as ambident nucleophile to furnish N,C-(III) and O,C-cross-coupling products (VI) together with rearranged isomer of compound (II). -(IOFFE,

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