Reaction of p-menthadiene diepoxides with amines and sodium azide

descriptionPublicationkeyboard_double_arrow_right Article 01 Sep 1977 English Publisher:Springer Science and Business Media LLCJournal:Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, volume 26, pages 1,911-1,915 (issn: 0568-5230, eissn: 1573-9171,

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Authors: L. A. Mukhamedova; F. G. Nasybullina; M. I. Kudryavtseva;

doi: 10.1007/bf00924388

Reaction of p-menthadiene diepoxides with amines and sodium azide

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Abstract

1. p-Menthadiene diepoxides react with amines with opening of the 8,9-epoxide ring. Under mild conditions ethylamine and a mixture of p-menthadiene cis- and trans-diepoxides form a 3∶2 mixture of 8-hydroxy-9-(ethylamino)-1,2-epoxy-cis-p-menthane and 8-hydroxy-9-(ethylamino)-1, 2-epoxy-trans-p-menthane. Isopropylamine and diethylamine react with the trans-diepoxide only. 2. The reaction of p-menthadiene diepoxides with sodium azide involves opening of the 1,2-epoxide ring to form a 1∶1 mixture of trans-2-hydroxy-1-azido-8,9-epoxy-trans-menthane and trans-1-hydroxy-2-azido-8,9-epoxy-trans-p-menthane.

Related Organizations

Russian Academy of Sciences
Russian Federation
A.E. Arbuzov Institute of Organic and Physical Chemistry
Russian Federation

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