Novel reactions of ceph-3-ems

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).<br/><br/>A reverse Michael addition was attempted on the C-4 mono-adducts (M) and (N) and di-adducts (L) and (O).<br/><br/>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).<br/><br/>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.<br/><br/>Numerous attempts at a Cope rearrangement on ceph-2-em sulphoxide (G) and sulphide (H) failed.<br/><br/>De-esterification reactions of the new ceph-3-ems to their corresponding acids were unsuccessful.

Name dc:type.qualificationname

PhD

Level dc:type.qualificationlevel

Doctoral Thesis

Grantor dc:publisher.institution

University of Abertay Dundee

Year dc:date.issued

1995

Author dc:creator

• Torrance, Jacqueline

Advisor dc:contributor.advisor

• Bremner, David

Language dc:language

eng

Identifier

oai:rke.abertay.ac.uk:studenttheses/4c9a614b-0619-42af-869f-bad5a5ae915f

OAI identifier oai:identifier

oai:rke.abertay.ac.uk:studenttheses/4c9a614b-0619-42af-869f-bad5a5ae915f