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Lithiation of 1-Aminonaphthalene, and Preparation of Some 8-Substituted 1-Tritionaphthalenes by C. Eaborn; P. Golborn; R. Taylor is a Chemistry article available to read on EtoBox.

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## SHORT COMMSJN ICATION Lithiation of 1-aminonaphthalene, and preparation of some S-substituted 1-tritionaphthalenes Treatment of l-methoxynaphthalene with n-butyllithium was recently shown to give up to 3.5 oA of S-lithio-1-methoxynaphthalene along with the expected Z-lithio compound'. We have found that 8-metallation also occurs (probably exclusively) when 1-aminonaphthalene is treated with n-butyllithium. Under our conditions, involving 50 hours' refluxing of the ethereal mixture of n-butyllithium and 1-aminonaphthalene in 3 : 1 mole ratio, it seems that less than 20% of C-lithio product is formed. For example, when such lithiation was followed by carbonation, 8-amino-1-naphtholactam was obtained in 10% yield and 80% of the 1-aminonaphthalene was recovered unchanged. Lithiation followed by addition of a known amount and activity of tritiated water gave tritio-1-aminonaphthalene. The amino group was then removed by a method which should cause no significant loss of tritium attached to the 8-carbon atom. 8-Tritio-naphthalene was also prepared by cross-metallation of 1-bromonaphthalene with n-butyllithium followed by similar treatment with tritiated water, and the relative activit

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Author

C. Eaborn; P. Golborn; R. Taylor

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

1967

Language

EN

Field

Chemistry (Physical Sciences)