Journal of Organic Chemistry p. 1736 - 1743 (1989)
Update date:2022-08-02
Topics:
Warshaw, James A.
Gallis, David E.
Acken, Bruce J.
Gonzalez, Orestes J.
Crist, DeLanson R.
A general method was developed for the synthesis of acyclic α-alkoxynitrones (imidate N-oxides), a relatively new class of compounds.Regioselective alkylation of hydroxamic acids under neutral conditions with alkyl trifluoromethanesulfonates (triflates) gave nitrone hydrotriflates, and deprotonation by one of three methods gave the rather unstable nitrones in overall yields from 4 to 85percent.A wide range of substitution was possible, with R = H, Me, or Ar, R1 = Me or t-Bu, and R2 = Me or Et.The reactivity of these nitrones toward examples
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