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
2002
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/187743
Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 27
  • ???jsp.display-item.citation.isi??? 26
social impact