Novel reactions of ceph-3-ems

  • Jacqueline Torrance

    Student thesis: Doctoral Thesis


    Michael additions and reactions with haloalkanes have demonstrated the synthetic usefulness of the C-2 and C-4 anions in ceph-3-em sulphides and sulphoxides for the formation of a range of novel compounds (A-H). Other compounds prepared from similiar reactions include (I-O).

    A reverse Michael addition was attempted on the C-4 mono-adducts (M) and (N) and di-adducts (L) and (O).

    Determination of the configuration of the di-adducts (F) and (I) was accomplished by de-esterification followed by decarboxylation and resulted in the novel ceph-3-em (P).

    Conversion of (J) and (K) into novel ceph-3-ems (Q) and (R) bearing C-2 exocyclic bond systems via a Pummerer rearrangement is described. Attempts at a Pummerer rearrangement of (D) and (E) failed.

    Numerous attempts at a Cope rearrangement on ceph-2-em sulphoxide (G) and sulphide (H) failed.

    De-esterification reactions of the new ceph-3-ems to their corresponding acids were unsuccessful.
    Date of AwardJun 1995
    Original languageEnglish
    SupervisorDavid H. Bremner (Supervisor)

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