The synthesis and chemistry of strained bicyclic systems Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/pk02cd49z

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  • 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.
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  • description.provenance : Submitted by Kevin Martin (martikev@onid.orst.edu) on 2014-04-09T17:02:24Z No. of bitstreams: 1 ScerboLouis1968.pdf: 1749749 bytes, checksum: 2ef3a570f89ead302269944943fb432e (MD5)
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