1, 5-Dibenzyl-2, 3, 4, 4a, 5, 6, 7, 8 (or 2, 3, 4, 5, 6, 7, 8, 8a)-octahydrocyclobuta [1, 2-b : 3, 4-b'] dipyridin-1-ium halide (IIb) was reduced in different conditions to give six kinds of products of which structures except VI were elucidated. Catalytic hydrogenation of IIb in the presence of platinum afforded 1, 5-dibenzylper-hydrocyclobuta [1, 2-b : 3, 4-b'] dipyridine-A (III), 1, 1'-dibenzyl-epi-2, 3'-bipiperidine (IV), 1, 1'-dibenzyl-2, 3'-bipiperidine (V), N, N-dibenzyl-4-methyl-1, 9-nonanediamine (VII), and C
24H
34N
2 (VI). By reduction of IIb with sodium borohydride in methanol, III, IV, and V were formed, while by the same operation in tetrahydrofuran instead of methanol, III and its isomer-B (VIII) were produced.
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