The Journal of Organic Chemistry

Metal-ammonia reduction and reductive alkylation of N-alkylnaphthalenesulfonamides. A new route to substituted naphthalenes

HJE Loewenthal, L Gottlieb

Index: Loewenthal, H. J. E.; Gottlieb, L. Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2631 - 2641

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Citation Number: 10

Abstract

Conditions have been found for 1P-reduction of aromatic sulfonamides (conveniently monitored by electrical conductivity), using metala in THF/liquid ammonia on the preformed N-lithium salta (BuLi), without concomitant CS reductive cleavage. The resulting 1, 4-dihydro compounds could be alkylated, either in situ (in the case of simple unfunctionalized halides only) or, following isolation, after further N-alkylation and then forming the monoanion, or ...