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

N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pK a values of these N-substitu...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 65; no. 14; pp. 4370 - 4374
Main Authors Brosse, Nicolas, Pinto, Maria-Fatima, Jamart-Grégoire, Brigitte
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.07.2000
Amer Chemical Soc
Subjects
Chemical and Process Engineering
Chemical Sciences
Chemistry
Chemistry, Organic
Engineering Sciences
Materials
Organic chemistry
Physical Sciences
Polymers
Science & Technology
SUBSTITUTED HYDRAZINES
REAGENT
ALCOHOLS
ACID
DIMETHYL-SULFOXIDE
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Summary:N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pK a values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.
Bibliography:istex:132F772C3D3697B1E4D9CFF26D0F62222BFE4093
ark:/67375/TPS-LWK2FR5J-V
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo000225s