Synthesis of Substituted 2,5-Dihydrothiophene-2-Carboxylic Acids by Lithium/Ammonia Reduction

Autor:	Walter G. Blenderman, Madeleine M. Joullié
Rok vydání:	1981
Předmět:	Reaction conditions Allylic rearrangement Chemistry Organic Chemistry chemistry.chemical_element Reaction product Metal Ammonia chemistry.chemical_compound visual_art Reductive cleavage visual_art.visual_art_medium Organic chemistry Lithium
Zdroj:	Synthetic Communications. 11:881-888
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397918108065742
Popis:	The lithium/ammonia reduction of thiophene-2-carboxylic acid (1) has been reported independently by different investigators1,2 to afford 2,5-dihydrothiophene-2-carboxylic acid (2) as the major product. The isolation of this compound, however, is made difficult by its susceptibility to further reduction or reductive cleavage under the reaction conditions employed. Compounds with allylic carbon-sulfur bonds, for example, are readily cleaved in metal/ammonia solutions3a,b to give the corresponding mercaptans. With 2, reductive cleavage affords cis-5-mercapto-3-pentenoic acid (3) which, in fact can be made the exclusive reaction product from 1 by appropriate modification of reaction conditions.
Databáze:	OpenAIRE
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