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Theoretical and experimental investigation of stereoselective iodolactonisation.

Bissmire, Stewart. 2006. Theoretical and experimental investigation of stereoselective iodolactonisation. PhD Thesis, Cardiff University.

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Abstract

Lactonizations are important steps in many synthetic sequences. Substrate-controlled reactions that use chiral auxiliaries or chiral alkenes have already been studied in depth. This study focuses on stereoselective reagent-controlled iodolactonizations, by application of a new method that uses complexes of iodine monochloride and various donor molecules. (/)-l,2,3,4-Tetrahydro-l-naphthylamine and other amines with similar structures were synthesized and found to be efficient in the iodocyclization of 4-aryl-4-pentenoic acids and other similar substrates. Calculations were performed on complexes of ( )-l,2,3,4-tetrahydro-l-naphthylamine with XC1 (X=I, H) to identify possible reactive species in these iodocyclizations. Various levels of theory were employed, including B3LYP/6-31+G (d,p) using a modified SDD basis set for iodine.

Item Type: Thesis (PhD)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
ISBN: 9781303207891
Funders: EPSRC
Date of First Compliant Deposit: 30 March 2016
Last Modified: 09 Jan 2018 21:23
URI: http://orca.cardiff.ac.uk/id/eprint/56149

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