N,N-Diisopropiletilamina

La N,N-Diisopropiletilamina o base de Hünig, DIPEA o DIEA es un compuesto orgánico y amina. Es utilizado en química orgánica como una base. Debido a que su átomo de nitrógeno está apantallado por los dos grupos isopropilo y un grupo etilo, solo un protón es suficientemente pequeño para entrar y ser captado por el par electrónico libre del átomo de nitrógeno. Del mismo modo que la 2,2,6,6-tetrametilpiperidina, este compuesto es una buena base, pero un nucleófilo pobre, lo que lo hace un reactivo orgánico útil como base no nucleófila.

La base de Hünig es preparada tradicionalmente por la reacción de la diisopropilamina con sulfato de dietilo.[1]​

La base de Hünig forma un compuesto complejo heterocíclico denominado escorpionina, mediante una reacción con dicloruro de diazufre, catalizada por DABCO en una reacción "one-pot".[2]​

Base de Hünig en la síntesis de la escorpionina

La base de Hünig fue investigada para su uso como un reactivo selectivo en la alquilación de aminas secundarias a aminas terciarias por halogenuros de alquilo. Esta reacción orgánica es obstaculizada frecuentemente por una reacción lateral de cuaternización a la sal de amonio cuaternario, pero esto está evitado cuando está presente la base de Hünig.[3]​

La base de Hünig asiste las N-alquilaciones de aminas secundarias

Referencias

  1. ↑ Hünig, S.; Kiessel, M. (1958). «Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen». Chemische Berichte 91: 380-392. doi:10.1002/cber.19580910223. 
  2. ↑ From Hünig's Base to Bis([1,2]dithiolo)-[1,4]thiazines in One Pot: The Fast Route to Highly Sulfurated Heterocycles W. Rees, Carlos F. Marcos,Cecilia Polo, Tomás Torroba,Oleg A. Rakitin Angewandte Chemie International Edition Volume 36, Issue 3 , Pages 281 - 283 2003 Abstract
  3. ↑ An efficient and operationally convenient general synthesis of tertiary amines by direct alkylation of secondary amines with alkyl halides in the presence of Huenig’s base Jason L. Moore, Stephen M. Taylor, and Vadim A. Soloshonok Arkivoc (EJ-1549C) pp 287-292 2005 Online Article Archivado el 4 de marzo de 2008 en Wayback Machine.

Enlaces externos

  • Company named after Hünig's base [1]
  • Scorpionine homepage [2][3]

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