European Journal of Chemistry

Comparative study of reactivity of (-)-R-carvone, (-)-R-linalool and (-)-(1S,4S)-camphor derivatives: Synthesis of new heterocycles

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Published: Sep 30, 2014
DOI: https://doi.org/10.5155/eurjchem.5.3.383-387.1029
Keywords:
Mentha, Artemisia, Lavandula, Terpenoids, Cycloaddition, Phenylnitrile oxide
Section
Research Article
Issue
Vol. 5 No. 3 (2014): September 2014
Dates
Received 2014-02-05
Accepted 2014-03-17
Published 2014-09-30


Main Article Content

Mohamed Rouani
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
Bouchra Rahmouni
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
Malika Chammache
Department of Chemistry, Heterocyclic Chemistry Laboratory, Faculty of Sciences, University Mohammed V Agdal, Rabat, BP1014, Morocco
Aziz El-Mebtoul
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
Abdelkader Ilidrissi
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco

Abstract

Reactivity comparison by 1,3-dipolar cycloaddition of the three dipolarophiles (-)-R-Carvone (I), (-)-R-Linalool (II) and derivative of (-)-(1S,4S)-camphor (III) has been studied. By reactions of p-chlorophenylnitrile oxide, new heterocycles are obtained by stereospecific reactions for cyclic Terpenoids I and III (regardless of the length of the side chain). However the aliphatic dipolarophile II gives two diastereoisomers. Terpenoids (-)-R-Carvone I (-)-R-Linalool II and (-)-(1S,4S)-Camphor 1 are isolated respectively from Moroccan species Mentha viridis (L.), Lavandula officinalis (L.) and Artemisia herba halba (Asso). The new heterocycles obtained were identified by combination of chromatographic and spectroscopic methods.


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(1)
Rouani, M.; Rahmouni, B.; Chammache, M.; El-Mebtoul, A.; Ilidrissi, A. Comparative Study of Reactivity of (-)-R-Carvone, (-)-R-Linalool and (-)-(1S,4S)-Camphor Derivatives: Synthesis of New Heterocycles. Eur. J. Chem. 2014, 5, 383-387.

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