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N-Boc-hydroxylamine is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts. It acts as a reagent for the synthesis of hydroxylamine derivatives t-butyl-N-(acyloxy)carbamates and N,O-diacylated N-hydroxyarylsulfonamides.
Precursor of O-substituted hydroxylamines, including the unstable O-acyl and O-sulfonylhydroxylamines which, having a good leaving group on nitrogen, are powerful aminating agents: J. Am. Chem. Soc., 82, 3133 (1960); Tetrahedron, 29, 1063 (1973); Synthesis, 140 (1972). For a review of O-mesitylenesulfonylhydroxylamine and related compounds, see: Synthesis, 1 (1977).
Pariente-Cohen, N.; Weitman, M.; Tania, N.; Major, D. T.; Gottlieb, H. E.; Hoz, S.; Nudelman, A. Acylation or phosphorylation of hydroxyurea unexpectedly takes place on N rather than on O, leading to the formation of amides instead of the expected esters. RSC Adv. 2015, 5 (31), 24038-24043.
Gini, A.; Segler, M.; Kellner, D.; Mancheño, O. G. Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines. Chem. Eur. J. 2015, 21 (34), 12053-12060.