Tetrahedron letters

Metal-ammonia reduction and reductive alkylation of naphthalene sulphonamides. A new route to substituted naphthalenes.

L Gottlieb, HJE Loewenthal

Index: Gottlieb, L.; Loewenthal, H. J. E. Tetrahedron Letters, 1988 , vol. 29, # 35 p. 4473 - 4476

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Abstract

Abstract Conditions have been found for the successful Birch reduction and reductive alkylation of N-alkyl arylsulphonamides, specifically in the naphthalene series. The derived C-alkylation products smoothly fragment on heating with re-aromatisation, affording a new specific route to 1-substituted naphthalenes starting from the 1-sulphonamides, and to both 2-mono-substituted and 2, 4-(or 1, 3-) disubstituted naphthalenes from the corresponding ...

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