The successive treatment of diallyl amine (1a) with an alkyl-lithium reragent leads to several trianionic derivatives (4a) in a regio-and stereo-selective manner; in the case of N-allyl-N-(methylallyl)amine (1b), the lithiation step is only observed in the methylallyl moiety of the amine; these trianions are characterized by reaction with deuterium oxide to yeild the corresponding deuteriated products (5).
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Barluenga et al. (1990) studied this question.
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