The Journal of Organic Chemistry

Preparation and utility of dianions from N-tert-butylthiophene-2-sulfonamide

SL Graham, TH Scholz

Index: Graham, Samuel L.; Scholz, Thomas H. Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4260 - 4263

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Citation Number: 26

Abstract

Metalation of N-tert-butylthiophene-2-sulfonamide with n-butyllithium occura competitively at the 3-and 5-position of the thiophene ring. Equilibration of the initial mixture of Carbanions or metalation with lithium dihpropylamide allows selective formation of the N, 5dilithiothiopheneulfonamide 7. This dianion is useful for the preparation of a number of 5- substituted thiophene-2-sulfonamides.