New heterocycles with hydrocarbon cage substituents

Copp, Steven B. (1995) New heterocycles with hydrocarbon cage substituents. Masters thesis, Memorial University of Newfoundland.

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Abstract

The proficiency with which main group (n≥3) π systems (e.g. the nitrile sulphides (C≡N⁺-S') and phosphaalkynes (C≡P)) imitate organic chemistry has been well documented. An investigation of the ability of main group π systems to be stabilized by mono- and di-substituted hydrocarbon cages (adamantane, bicyclo[2.2.2]octane) was undertaken. These types of compounds have not been extensively reported in the literature. Adamantyl-1,3,4-oxathiazol-2-one and bis-(3-Mesityl-1,2,4-oxazaphosphole)bicyclo [2.2.2]octane, have been prepared for the first time. The first X-Ray crystal structures of the oxathiazolone and oxazaphosphole heterocyclic rings will also be reported. The synthesis of precursors to these compounds will be presented along with full spectral characterisation. Attempts to generate a molecule containing two independent phosphaalkyne moieties will also be discussed.

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