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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

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

  • J. Caram , M. E. Martins , C. M. Marschoff , L. F. R. Cafferata and E. G. Gros
From the journal Zeitschrift für Naturforschung B
https://doi.org/10.1515/znb-1984-0722
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Treament of ( + )limonene with diluted perchloric acid in acetonitrile solution afforded (1 S ,5 R ,8 R ) 8-acetamido-2,4,4.8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate while the same reaction on ( - )β-pinene produced the (1 R ,5 S ,8 S ) enantiomer, and terpinolene gave the racemic mixture. The structure of 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.

Keywords: Ritter Reaction; ( + )Limonene; ( - )β-Pinene; Terpinolene; Stereospecific Synthesis
Received: 1983-11-28
Published Online: 2014-6-2
Published in Print: 1984-7-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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From the journal
Zeitschrift für Naturforschung B
Zeitschrift für Naturforschung B
Volume 39 Issue 7

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