Abstract
A limited amount of synthetic work has been carried out with silyl nitronates (silyl esters of nitronic acids). IR, UV, and variable temperature NMR spectra, as well as, a low temperature X-ray structure of a silyl nitronate have been reported [2]. The concentration independent variable temperature NMR behavior of these species is consistent with fast intramolecular migration of the silyl group between the two oxygens of the nitronate [2]. Although silyl nitronates are more thermally stable than the corresponding alkyl nitronates [1, 2], they readily undergo hydrolysis to regenerate the nitroalkanes. t-Butyldimethylsilyl nitronates are less susceptible to hydrolysis than trimethylsilyl nitronates [2].
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© 1983 Springer-Verlag Berlin Heidelberg
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Weber, W.P. (1983). Silyl Nitronates. In: Silicon Reagents for Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68661-0_5
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DOI: https://doi.org/10.1007/978-3-642-68661-0_5
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