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Silyl Nitronates in Organic Synthesis. Silylation of Secondary Nitro Compounds. Preparation of Nitroso Compounds and α,β-Unsaturated Aldehydes
Mukerji, Somir K.,Torssell, Kurt B. G.
, p. 643 - 648 (2007/10/02)
Secondary nitro compounds can be silylated by triethylamine and chlorotrimethylsilane in acetonitrile as solvent.The silyl nitronates add to olefins forming 3,3-disubstituted isoxazolidines, which can be rearranged to tertiary nitroso compounds.Addition of the secondary nitronates to acrylonitrile and subsequent treatment with fluoride ion leads to β,β-unsaturated aldehydes.
