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4 in DMSO, the only observed product was 2-fluoro-2-phenyl-1-ethanol, probably via reduction of a single ester moiety, followed by retro-aldol condensation, favored by the presence of the electronegative fluorine atom, and final reduction of the second ester moiety; retro-aldol reaction of a hydroxy ester under basic reductive conditions has been already observed (see Ref. 19g).
-
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30
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0345429076
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As a matter of fact, fluorinated diols showed a noticeable instability, both in acidic and (especially) basic conditions.
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0344567027
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Other chiral amines, like 1-naphthylethylamine (see Ref. 19c) were not assayed.
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