The Reactions of Some Thiophene Sulfonyl Derivatives

Thiophene-2-sulfonyl chloride has been allowed to react with 7 amines, hydrazine and sodium azide. The hydrazide was converted into 21 hydrazones. The azide reacts with cyclohexene, norbornene and triphenylphosphine. The sulfonyl chloride with chlorosulfonic acid gave a mixture of the 2,4- and 2,5-bis-sulfonyl chlorides (2:1). These were not separated by conversion to amides, azides, hydrazides, or hydrazones. 2-Carboxythiophene with chlorosulfonic acid gave a mixture of the 4- and 5-sulfonyl chlorides (9:1), conversion to amides and recrystallization gave the 4-sulfonamides. Chloro-sulfonation of 2-carboxamido- and 2-N,N-dimethylcarboxamidothiophene gave the 4-sulfonyl chlorides, characterized as amides, hydrazides and 18 hydrazones. Some N-arylthiophenesulfonamides were condensed with trichloromethylsulfonyl chloride. The i.r., n.m.r. and mass spectra of the various thiophenesulfonyl derivatives are discussed.