Record Details
The synthesis and chemistry of strained bicyclic systems
ScholarsArchive at Oregon State University
| Field | Value |
|---|---|
| Title | The synthesis and chemistry of strained bicyclic systems |
| Names |
Scerbo, Louis
(creator) Bond, F. Thomas (advisor) |
| Date Issued | 1968-03-29 (iso8601) |
| Note | Graduation date: 1968 |
| Abstract | A facile route to bicyclo(2.1.1)hexanes was developed involving the intramolecular photocyclization of 1, 5-hexadien-3-one to bicyclo(2.1.1)hexan-2-one. A study of the chemistry of bicyclo-(2.1.1)hexan-2-one was undertaken. Deuterium exchange and borohydride reduction demonstrated the strain present in the ketone. Further evidence was obtained from the failure to introduce substituents alpha to the carbonyl group, a usually facile reaction and a necessary step in desired ring contraction studies. After numerous unsuccessful attempts to introduce a double bond into the bicyclo(2.1.1) hexane system, a successful route to the parent bicyclo(2.1.1) hexene was achieved. The key step involved dehydrohalogenation of 2-bromobicyclo(2.1.1)hexane. Some preliminary studies of the olefin have been carried out and its thermolysis studied. |
| Genre | Thesis/Dissertation |
| Topic | Organic compounds -- Synthesis |
| Identifier | http://hdl.handle.net/1957/47439 |
