City Research Online

Abstract

A review of the literature on intramolecular cycloadditions is presented.

The cycloaddition reactions of substituted 2-pyridones are examined to elucidate the relative importance of steric and electronic factors for successful addition.

Intramolecular cycloadditions of unactivated olefins to oxazoles have been discovered. The primary adducts are not observed and only the annulated pyridine derivatives are isolated.

A novel rearrangement of 2-pentenyl oxazoles to give pyrrolyloxazole derivatives has been discovered and attempts to elucidate its mechanism are described.

Intermolecular cycloaddition reactions of oxazoles with olefinic and acetylenic dienophiles have been investigated to yield the expected pyridine and furan derivatives.

Molecular orbital parameters have been calculated using CNDO/2, MNDO and ab initio (Gaussian 70) methods, the relative merits of | these programmes have been evaluated by appeal to known experimentally determined values.

The usefulness of the Frontier Molecular Orbital theory when applied to cycloaddition reactions is considered.

Publication Type:	Thesis (Doctoral)
Subjects:	Q Science > Q Science (General) Q Science > QC Physics Q Science > QD Chemistry
Departments:	Doctoral Theses

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