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Fast and efficient preparation of Baylis-Hillman-derived (E)-allylic azides and related compounds in aqueous medium
Authors:Marcus M. Sá  ,Marcia D. Ramos,Luciano Fernandes
Affiliation:Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil
Abstract:A practical access to alkyl- and aryl-substituted (E)-2-(azidomethyl)alkenoates and related azido compounds from the corresponding allylic bromides in aqueous acetone is described. An alternative method to obtain the starting bromides based on heterogeneous catalysis under mild conditions was also investigated.
Keywords:Baylis-Hillman reaction   Allylic azides   Allylic bromides   [3,3]-Sigmatropic rearrangement   Aqueous solvents   Heterogeneous catalysis
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