Homolytic alkylation of chromones in micellar solution | Zendy

Engbersen J. F. J. | Zendy; Koudijs A. | Zendy; Van Plas H. C. Der | Zendy

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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.

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