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- W2007676670 abstract "Abstract The recent claim of Otsuji, Yutani and Imoto7 that both n-butyllithium and phenyllithium gave isolable 1,4-adducts with lepidine (4-methylquinoline) has been reinvestigated. Such adducts were reportedly captured in the form of their N-ethoxycarbonyl derivatives. In the present study these same N-ethoxycarbonyl derivatives have been prepared and examined by NMR and IR spectroscopy. Moreover, the corresponding N-(ethoxycarbonyl)-n-butyldihydro and N-(ethoxycarbonyl)phenyldihydro derivatives have now been prepared from 2-deuteriolepidine. An analysis of the spectroscopic data leads to the clear conclusion that all such derivatives are really 2-substituted-1,2-dihydrolepidines. Consequently, all the discussion published in ref. 7, concerning a 1,4-addition of organolithium reagents to the quinoline nucleus and the subsequent rearrangement to the 1,2-adduct, becomes unfounded." @default.
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- W2007676670 modified "2023-09-23" @default.
- W2007676670 title "Reinvestigation of apparent 1,4-addition and rearrangement in the reactions of quinolines with organolithium compounds" @default.
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- W2007676670 doi "https://doi.org/10.1016/s0022-328x(00)83319-7" @default.
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