N,N di-2-chloroethyl 4-amino 2-methyl 1-methoxy naphthalene is labelled with 14C on two different positions: uniformly on the four carbons of the dichloroethyl group by means of radioactive ethylene oxide; and on the carbon of the methoxy group
NMR and calculational studies on the regioselective lithiation of 1-methoxynaphthalene
1-Methoxynaphthalene (1) undergoes regioselective lithiation in position 2 (n-BuLi/TMEDA) or in position 8 (t-BuLi), respectively. The detected formation of a n-BuLi/1 complex (1:1 n-BuLi/1 mixture) appears to have only minor influence on the regioselectivity (both products are obtained). The exchange of hydrogen atom H2 by deuterium results in a remarkably reduced reaction rate for the lithiation with n-BuLi in THF-d8. This isotope effect and the formation of the thermodynamically less favorable 2-lithio compound suggest a kinetically controlled mechanism. The lack of an isotope effect for the reaction of 8-deuterio-1-methoxynaphthalene with t-BuLi and the formation of the thermodynamically preferred 8-lithiated product indicate a thermodynamically controlled mechanism. Slow conversion of the 2- into the 8-lithiated species (at higher temperatures) gives further evidence that n-BuLi and t-BuLi afford the kinetically and thermodynamically preferred products, respectively.
Functionalization of Aromatic Molecules Using HOF*CH3CN and CH3OF
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Kol, Moshe,Rozen, Shlomo
p. 1593 - 1595
(2007/10/02)
Preparation of 2-Alkyl-1-naphthols and 1-Alkyl-2-naphthols
C-Alkylation of 1-naphthol and 2-naphthol with n-butyllithium and dialkyl sulphate easily afford 2-alkyl-1-naphthols and 1-alkyl-2-naphthols respectively in relatively good yields.
Saidi, Mohammad R.
p. 474
(2007/10/02)
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