Easy Access to N,N-Bis(but-3-enyl)-, N-Allyl-N-(but-3-enyl)-, and N-(But-3-ynyl)-N-(but-3-enyl)-amines

Easy Access to N,N-Bis(but-3-enyl)-, N-Allyl-N-(but-3-enyl)-, and N-(But-3-ynyl)-N-(but-3-enyl)-amines

N,N-Bis(but-3-enyl)amines 5a − i were prepared in overall 74% yield from 1-(triphenylphosphoroylideneaminoalkyl)benzotriazole using an aza-Wittig reaction with aldehydes followed by a double Grignard reaction with allylmagnesium bromide. Use of vinyl or 1-propynylmagnesium bromide and allylmagnesium...

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Veröffentlicht in:Journal of organic chemistry 2002-10, Vol.67 (21), p.7530-7532
Hauptverfasser: Katritzky, Alan R, Nair, Satheesh K, Silina, Alina
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung:N,N-Bis(but-3-enyl)amines 5a − i were prepared in overall 74% yield from 1-(triphenylphosphoroylideneaminoalkyl)benzotriazole using an aza-Wittig reaction with aldehydes followed by a double Grignard reaction with allylmagnesium bromide. Use of vinyl or 1-propynylmagnesium bromide and allylmagnesium bromide in a sequential fashion also formed the expected doubly unsaturated amines 9a , b and 12, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020118t