Fischer hydrazinocarbene complexes are oxidized to hydrazides in high yields by three different methods. Under biphasic conditions, Fischer hydrazinocarbene complexes are oxidized in 28-92% yields with calcium hypochlorite in water and Et acetate in the presence of potassium phosphates as buffering agents and tetrabutylammonium hydrogen sulfate as a phase-transfer catalyst. Oxidn. of Fischer hydrazinocarbene complexes with iodine generated in situ from sodium perborate and potassium iodide in water/ethyl acetate in the presence of potassium phosphates yields hydrazides in 84-96% yields, including particularly sensitive hydrazides derived from aldol or Michael addn. reactions. In a water/ethyl acetate mixt., iodine could also be used directly as the oxidant with sodium bicarbonate as the base to give hydrazides in 83-88% yields. The discussed methods circumvent the undesired oxidn. of hydrazides seen with previous oxidn. methods

New Methodologies for the Oxidation of Fischer Carbene Complexes: Synthesis of Hydrazides / D. Perdicchia, E. Licandro, S. Maiorana, B. Vandoni, C. Baldoli. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 4:5(2002), pp. 827-830.

New Methodologies for the Oxidation of Fischer Carbene Complexes: Synthesis of Hydrazides

D. Perdicchia
Primo
;
E. Licandro
Secondo
;
S. Maiorana;
2002

Abstract

Fischer hydrazinocarbene complexes are oxidized to hydrazides in high yields by three different methods. Under biphasic conditions, Fischer hydrazinocarbene complexes are oxidized in 28-92% yields with calcium hypochlorite in water and Et acetate in the presence of potassium phosphates as buffering agents and tetrabutylammonium hydrogen sulfate as a phase-transfer catalyst. Oxidn. of Fischer hydrazinocarbene complexes with iodine generated in situ from sodium perborate and potassium iodide in water/ethyl acetate in the presence of potassium phosphates yields hydrazides in 84-96% yields, including particularly sensitive hydrazides derived from aldol or Michael addn. reactions. In a water/ethyl acetate mixt., iodine could also be used directly as the oxidant with sodium bicarbonate as the base to give hydrazides in 83-88% yields. The discussed methods circumvent the undesired oxidn. of hydrazides seen with previous oxidn. methods
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187743
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