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Barbier‐Type Reactions of Cyclic Acid Anhydrides and Keto Acids Mediated by an SmI 2 ‐(NiI 2 ‐Catalytic) System – Preparation of Disubstituted Lactones
Author(s) -
Machrouhi Fouzia,
Pârlea Elena,
Namy JeanLouis
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2431::aid-ejoc2431>3.0.co;2-7
Subject(s) - chemistry , catalysis , yield (engineering) , hydrolysis , samarium diiodide , samarium , organic chemistry , alkyl , carboxylate , medicinal chemistry , succinic anhydride , materials science , metallurgy
Cyclic acid anhydrides (succinic and glutaric anhydrides and some of their derivatives) undergo fast Barbier‐type reactions mediated by samarium diiodide in the presence of catalytic amounts of nickel diiodide (1 mol‐% with respect to SmI 2 ), to give disubstituted lactones in high yields. Without NiI 2 no reaction occurs. Various alkyl and allyl iodides can be used. In these reactions the formation of a samarium keto carboxylate intermediate is likely; as a matter of fact, keto carboxylic acids react under similar conditions to also yield disubstituted lactones. It is demonstrated that lactonisation occurs during hydrolysis of the reaction.