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3/t-BuOH/benzene/AIBN) was tested in the reduction of bromoadamantane. Gas chromatographic analysis of the reaction mixture after 1 h at 80 °C showed 99% yield of adamantane (using naphthalene as internal standard). Sodium cyanoborohydride alone does not reduce bromoadamantane under these conditions, therefore an organotin hydride formed in situ is probably the active reducing agent.
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31
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0037695362
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note
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2 successfully afforded clean 2c.
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0038371548
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1H NMR spectrum, which correlate with a singlet at 0.57 ppm (18H). This byproduct, probably the result of β-elimination at the germanium center with loss of isobutene, was never isolated and fully characterized, but it was found in small amounts in almost every reaction condition employed.
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0038371547
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3SnH in the presence of variable amounts of
-
-
-
-
48
-
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0037695360
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note
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-1a (from 0.1 up to 1 equiv). In all cases, the reduced product 16 was obtained as racemic, indicating that if 1a takes part in the hydrogen abstraction step it does so without any stereoselectivity. This is expected since the structure of 1a is not as rigid and sterically demanding as that of 7a.
-
-
-
-
49
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0038709852
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note
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3 resonances.
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