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Title: New cyclisations of iminyl radicals generated by flash vacuum pyrolysis
Author: Ieva, Maria
ISNI:       0000 0004 2745 9540
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2012
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The formation of iminyl radicals from a range of precursors, including hydrazone imines and oxime ethers, under FVP conditions is well documented in the literature.1 Once formed, the iminyl radical can undergo cyclisation onto various aromatic ring systems including phenyl rings, thiophenes and furans to form new fused aromatics.2 The aim of this thesis was to expand the scope of cyclisation of iminyl radical onto pyrrole-type rings and 2-azole rings, generating novel heterocyclic cores via pyrolysis of the corresponding oxime ether precursors. In addition, the cyclisation of iminyl radicals onto C-C double bonds was investigated and afforded isoquinolines shown in Scheme II, providing a new way to synthesise these heterocyclic cores. Mechanistic predictions were supported by DFT calculations in which the thermodynamics and kinetics of the systems were established and the products of iminyl cyclisation reactions were characterised using a range of 2D NMR experiments.
Supervisor: Mcnab, Hamish; Hulme, Alison Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: iminyl radicals ; FVP ; Flash Vacuum Pyrolysis