Schmidt reaction of 4-substituted adamantanones |
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Authors: | Helmut Duddeck Dino Brosch Gudrun Koppetsch |
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Affiliation: | Ruhr-Universität Bochum, Abteilung für Chemie Postfach 10 21 48, D-4630 Bochum 1, FRG |
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Abstract: | The Schmidt reaction of various 4a - and 4e -substituted adamantanones has been investigated. It is shown that the direction of the nitrogen insertion is not dominated by inductive substituent influences. The main reaction pathway involves the diazoiminium ion 3 and the intermediates 4 and 5 which prefer different reactions: 4 undergoes mainly fragmentation (8 and 9) whereas 5 gives mainly water addition products (7). The recyclisation of 8 and 9 is highly regloselective. The structure determinations of the products are based on their 1H and 13C NMR data. |
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