The synthesis of a novel, cage spiro-oxetane was carried out. Pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-8- one (PCUD-8-one) undergoes one-carbon homologation to a mixture of endo- and exo- PCUD-carboxaldehydes which then are converted into 8,8-bis(hydroxymethyl)PCUD. The monotosylate obtained via reaction of 8,8- bis(hydroxymethyl)PCUD with tosyl chloride(1 equivalent) reacts with sodium hydride to afford the corresponding spiro-oxetane via intramolecular Williamson reaction. Six new substituted heptacyclo[6.6.0.0^2,6.0^3,13.0^4,11. 0^5,9.0^10,14]tetradecanes (HCTD) were synthesized. These compounds will be used as substrates in a photoelectron spectroscopic study. The ring-expansion reaction of PCUD-8-one with ethyl diazoacetate in the presence of BF_3:OEt_2 was performed. The major product was converted into an alcohol, and the structure of the 3,5-dinitrobenzoate of this alcohol was elucidated by single crystal x-ray structural analysis.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc500575 |
| Date | 08 1900 |
| Creators | Ren, Chien-Tai |
| Contributors | Marchand, Alan P., Brady, William Thomas |
| Publisher | University of North Texas |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | iv, 59 leaves : ill., Text |
| Rights | Public, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved., Ren, Chien-Tai |
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