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Reaction of Coumarins with Superoxide Anion Radical (O 2 ): Facile Entry to o‐Coumarinic Acid Systems
Author(s) -
Frimer Aryeh A.,
Aljadeff Gladis,
GilinskySharon Pessia
Publication year - 1986
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198600007
Subject(s) - chemistry , saponification , coumarin , hydrogen atom abstraction , iodide , superoxide , ion , organic chemistry , medicinal chemistry , photochemistry , combinatorial chemistry , hydrogen , enzyme
Coumarins 1–5 were reacted with O 2 in aprotic media. The course of the reaction was followed by using methyl iodide to “Cap” (trap) the oxy‐anions generated. Abstraction of the enolic hydrogen (where available) proved to be the most facile process followed by “saponification” of the lactone linkage. The cis ‐stereochemistry of the original coumarin was maintained allowing easy access to a variety of o‐coumarinic acid systems.