Rearrangements of Penicillin Sulfoxides. 1

Abraham Nudelman, Ronald J. McCaully

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Penicillin sulfoxides are converted to 3-halo-3-methylcepham-4-carboxylic acid esters or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in the polyhaloalkane solvent in the presence of an equimolar amount of a neutral or basic catalyst, respectively. Basic catalysts such as pyridine or 4-picoline afford cephem derivatives, whereas the quaternary ammonium salts bring about the formation of 3-halocepham derivatives.

Original languageEnglish
Pages (from-to)2887-2890
Number of pages4
JournalJournal of Organic Chemistry
Issue number17
StatePublished - 1 Aug 1977
Externally publishedYes


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