Identification of a product of the Friedel-Crafts cyclization of β -(3- cyclohexenyl) propionyl chloride Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/k3569858r

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  • An improved procedure for the preparation of β-(3-cyclohexenyl) propionic acid from 4-vinylcyclohexene was developed. The Friedel-Crafts cyclization of β-(3-(3-cyclohexenyl) propionyl chloride with aluminum chloride was shown to give one bicyclic chlorine containing ketone in 41% yield. This ketone was identified by a combination of spectral and chemical methods as a mixture of exo- and endo-6-chlorobicyclo[3.3.1] nonan-2-ones. Useful synthetic procedures for the conversion of this ketone to 6-bicyclo[3.3.1]-nonen-2-one and to 2-bicyclo[3.3.1] nonanols were developed. A logical route to 6-chlorobicyclo[3.3.1] nonan-2-one from β-cyclohexenyl) propionyl chloride must involve 2-oxo-8-bicyclo-[3.31] nonyl carbonium ion as an intermediate. In support of this idea it was shown that 8-chlorobicyclo[3.3.1] nonan-2-one can be converted to 6-chlorobicyclo[3.3.1] nonan-2-one under the conditions of the Friedel-Crafts cyclization.
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  • description.provenance : Approved for entry into archive by Katy Davis(kdscannerosu@gmail.com) on 2014-03-05T19:25:49Z (GMT) No. of bitstreams: 1 McEwenTerryE1969.pdf: 949973 bytes, checksum: 8f60fd1a09fc6688ef63c246846fbeb2 (MD5)
  • description.provenance : Approved for entry into archive by Katy Davis(kdscannerosu@gmail.com) on 2014-03-05T19:23:24Z (GMT) No. of bitstreams: 1 McEwenTerryE1969.pdf: 949973 bytes, checksum: 8f60fd1a09fc6688ef63c246846fbeb2 (MD5)
  • description.provenance : Made available in DSpace on 2014-03-05T19:25:49Z (GMT). No. of bitstreams: 1 McEwenTerryE1969.pdf: 949973 bytes, checksum: 8f60fd1a09fc6688ef63c246846fbeb2 (MD5) Previous issue date: 1968-05-29
  • description.provenance : Submitted by Katy Davis (kdscannerosu@gmail.com) on 2014-03-05T19:22:32Z No. of bitstreams: 1 McEwenTerryE1969.pdf: 949973 bytes, checksum: 8f60fd1a09fc6688ef63c246846fbeb2 (MD5)

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