Synthesis of substituted N-hydroxyureas via the in situ generation of t-butoxy isocyanate

…, BD Leskiw, ML Emery, ME McGahan, MP McCourt…

Index: Krause, Josef G.; Leskiw, Brian D.; Emery, Michelle L.; McGahan, Megan E.; McCourt, Mary P.; Priefer, Ronny Tetrahedron Letters, 2010 , vol. 51, # 27 p. 3568 - 3570

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Abstract

Treatment of primary and secondary amines with tert-butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxyureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method allows for the synthesis of both mono and disubstituted N- hydroxyureas.