I. Reductive dimerization of pentacyclo[5.4.0.0.^2,6.0^3,10.0^5'9]undecane-8-one-(PCU-8-one, 53) affords a mixture of meso and d,l pinacols (55a and 55b respectively). Acid promoted rearrangement of 55a and 55b conceivably can proceed with migration of C(7)-C(8) and/or C(8)-C(9) to form the corresponding pinacolone(s). In our hands, acid promoted rearrangement of 55a and 55b each proceeds with exclusive migration of C(7)- C(8) bond, thereby affording 58a and 59a respectively. Mechanistic features of this rearrangement are discussed.
II. 4,7,1 l-trimethylpentacyclo[6.3.0.0.^2,6.0^3,l0.0^5,9]undecane-exo-4,exo-7-diol
(23a) was successfully synthesized. This diol crystallizes in a helical tubuland lattice although its molecular structure does not possess C2 rotational symmetry.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc277859 |
| Date | 05 1900 |
| Creators | Liu, Zenghui |
| Contributors | Marchand, Alan P., Bott, Simon G. |
| Publisher | University of North Texas |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | vii, 87 leaves : ill., Text |
| Rights | Public, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved., Liu, Zenghui |
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