Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate

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Treament of ( + )lim onene with diluted perchloric acid in acetonitrile solution afforded (1S, 5R, 8R) 8-acetam ido-2,4,4.8-tetram ethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate while the same reaction on ( — )β-pinene produced the (1S, 5R, 8R) enantiom er, and terpinolene gave the racemic mixture....

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Detalles Bibliográficos
Autores principales: Caram, José Alberto, Martins, María Elisa, Marschoff, Carlos Miguel, Cafferata, Lázaro F. R.
Formato: Articulo
Lenguaje:Inglés
Publicado: 1984
Materias:
Química
Ritter Reaction
(+)Limonene
( -)β-Pinene
Terpinolene
Stereospecific synthesis
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/120779
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
Descripción
Sumario:Treament of ( + )lim onene with diluted perchloric acid in acetonitrile solution afforded (1S, 5R, 8R) 8-acetam ido-2,4,4.8-tetram ethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate while the same reaction on ( — )β-pinene produced the (1S, 5R, 8R) enantiom er, and terpinolene gave the racemic mixture. The structure o f the product is proposed on basis of its physical and spectroscopic (IR , ¹H and ¹³C NMR, MS) properties and its formation involves a Ritter reaction between the monoterpene and acetonitrile.

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