Date of Award


Degree Type


Degree Name

Master of Science (MS)

Author's Department


First Advisor

David H. Buchanan


Reactions of several phenyl ethers and an ester with pyridine hydrogen iodide were examined under various conditions as model studies for the recently reported molecular weight reduction of a fraction of Illinois No. 6 coal by hydrogen iodide in pyridine at 50°.

No ether or ester cleavage was observed at 60-80° in pyridine, acetonitrile, ethanol or the absence of solvent. Sealed tube reactions at 210° resulted in cleavage to phenol plus various hydrocarbon and alkyl halide products. Pyridine and benzyl phenyl ether at 210° produced no cleavage in the absence of hydrogen iodide.

Syntheses of crystalline pyridine hydrogen iodide and pyridine hydrogen bisulfate as well as cyclohexyl phenyl ether are described.

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Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.

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