Borohydride and cyanoborohydride reduction of thioimonium salts. A convenient route for transformation of amides to amines

RJ Sundberg, CP Walters…

Index: Sundberg, Richard J.; Walters, Claudia Powers; Bloom, Jonathan D. Journal of Organic Chemistry, 1981 , vol. 46, # 18 p. 3730 - 3732

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Citation Number: 36

Abstract

Finally, we examined several vinylogous thioamides. The requisite 8-aroylenamines were prepared from acetophenones as described by Gupton et d.* and converted to the thiones by reaction with PzS6 in ben~ ene.~ Methylation was rapid with methyl iodide. The resulting salts were reduced in 5040% yields to the vinyl sulfides 8a-8c.

~52%

~78%

~44%

~65%

~49%

~43%

~65%

~75%

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