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The Synthesis of 4‐Decarboxy‐4‐phosphono‐ O ‐2‐isooxacephems, ‐isopenams and ‐isooxacephems Containing Phosphorus at the 3‐Position
Author(s) -
Hakimelahi Gholam Hosein,
Just George
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650505
Subject(s) - chemistry , sulfur , phosphonate , ylide , reagent , phosphorus , potassium , autocatalysis , medicinal chemistry , group (periodic table) , stereochemistry , catalysis , organic chemistry
Abstract Two new types of iso‐oxacephems have been synthesized in which a phosphonate group replaces either the carboxyl group or C(3). The latter compound exists as a stable trialkoxyphosphonium ylide. Potassium thioacetate and O 2 in DMF are transformed in an autocatalytic, probably sulfur‐catalyzed process to CH 3 COOK and sulfur; the latter two reagents are sufficient to transform the methanesulfonate 7 to the isopenam 15 .