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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 2
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Original Articles

Synthesis of N,N-Dimethyl-3-Noradamantanamine-N-Oxide

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Pages 245-251 | Received 06 Aug 1992, Published online: 23 Sep 2006
 

Abstract

N,N-dimethyl-3-noradamantanamine-N-oxide (5), a potential precursor of tricyclo[3.3.1.03,7]nonan-3(7) ene, has been synthesized in two steps involving an Eshweiler-Clark reaction of 3-noradamantanamine followed by m-chloroperoxybenzoic acid oxidation of the resulting N,N-dimethylamino-3-noradamantanamine (4). Thermolysis of 5, however, unexpectedly gave the reduced N,N-dimethylamino product, 4.

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