NOVEL ALKOXYLATIONS OF CEPHALOSPORINS BY CERIUM(IV) SALTS AND BY ELECTRO-OXIDATIVE PROCEDURES

Electrolyses of cephalosporins in methanol-tetrahydrofuran mixtures in the presence of tetraethylammonium tosylate provide useful syntheses of the corresponding 2-methoxy derivatives [(2), (3b), and (6)]. The same derivatives are produced when the cephalosporins are treated with cerium(IV) ammonium...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 7; pp. 1685 - 1688
Main Authors PATTENDEN, G, STAPLETON, A, HUMBER, DC, ROBERTS, SM
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1988
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Electrolyses of cephalosporins in methanol-tetrahydrofuran mixtures in the presence of tetraethylammonium tosylate provide useful syntheses of the corresponding 2-methoxy derivatives [(2), (3b), and (6)]. The same derivatives are produced when the cephalosporins are treated with cerium(IV) ammonium nitrate (CAN) in methanolic tetrahydrofuran. Alkoxylations of the cephalosporin (1) by CAN or by the electro-oxidative procedure, in the presence of ethanol, propan-2-ol, or benzyl alcohol, lead to the corresponding 2-ethoxy (7a), 2-isopropoxy (7b), and 2-benzyloxy derivatives.
ISSN:1472-7781
0300-922X
1364-5463
DOI:10.1039/p19880001685