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Homolytic alkylation of chromones in micellar solution
Author(s) -
Engbersen J. F. J.,
Koudijs A.,
Van Plas H. C. Der
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190604
Subject(s) - chemistry , homolysis , peroxydisulfate , chromone , alkylation , aqueous solution , sodium dodecylbenzenesulfonate , medicinal chemistry , catalysis , ammonium , organic chemistry , radical
Treatment of an aqueous solution of chromone, the detergent sodium dodecylbenzenesulfonate, silver nitrate and an alkanoic acid, with ammonium peroxydisulfate gives 2‐R‐chromone [R = i ‐C 3 H 7 (47%), R = t ‐C 4 H 9 (65%) and R = 1‐adamantyl (78%)]. In addition 2‐R‐4‐chromanone [R = i ‐C 3 H 7 (40%), R = t ‐C 4 H 9 (5%) and R‐1‐adamantyl (10%)] is formed. It is proposed that the reaction involves as intermediate the relatively stable 2‐R‐4‐chromanon‐3‐yl radical and that the detergent has a micellar catalytic activity on the free radical alkylation process.