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New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

Nicolas Brosse, Maria-Fatima Pinto and Brigitte Jamart-Grégoire*

*Faculté des Sciences, Université H. Poincaré Nancy I, Bld. des Aiguillettes BP 239 F-54506 Vandoeuvre-lès-Nancy France, Email: brigitte.jamarteeigm.univ-lorraine.fr

N. Brosse, M.-F. Pinto, B. Jamart-Grégoire, J. Org. Chem., 2000, 65, 4370-4374.

DOI: 10.1021/jo000225s (free Supporting Information)


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Abstract

N-acyl- and N-alkoxycarbonylaminophthalimides are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.

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Key Words

Mitsunobu reaction, hydrazines, dephthaloylation


ID: J42-Y2000