Graduate Thesis Or Dissertation
 

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

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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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