Thermal rearrangement of oxygen-containing {omicron}-allyltoluene derivatives
For several years, workers in the Trahanovsky group have been studying the gas phase thermal reactions of simple organic molecules. The FVP of {Omicron}-allyltoluene involves a novel rearrangement that is proposed to involve a diradical produced by intramolecular hydrogen-atom transfer which undergoes intramolecular coupling to give 2-methylindan. Studies of this rearrangement have been extended to other systems. The two papers in this thesis describe studies of the flash vacuum pyrolysis (FVP) of oxygen-containing {omicron}-allyltoluene derivatives. In the first chapter of this thesis, the results from o-allylbenzaldehyde and related compounds are examined in terms of the intramolecular hydrogen-atom transfer diradical/coupling mechanism. A mechanism which involves an enol intermediate generated by an oxa-1,5 H shift is proposed for formation of naphthalene from the FVP of o-allylbenzaldehyde. In the second chapter more limitations of the formation of the diradicals is revealed.
- Research Organization:
- Ames Lab., IA (United States)
- Sponsoring Organization:
- USDOE, Washington, DC (United States)
- DOE Contract Number:
- W-7405-ENG-82
- OSTI ID:
- 57238
- Report Number(s):
- IS-T--1721; ON: DE95010124
- Country of Publication:
- United States
- Language:
- English
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