Sekera, Michael H. (1982) Cationic cyclization involving a remote allene function in the trifluoroethanolysis of 5,6-heptadien-1-yl p-toluenesulfonate. Master's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechTHESIS:03282010-113717103
In order to determine whether a remote allene function would undergo intramolecular nucleophriftsubstitution, 5,6-heptadien-1-yl p-toluenesulfonate (14) was synthesized and solvolyzed. The major products of the trifluoroethanolysis of 14 were the cyclic trifluoroethyl ethers of 2-methylenecyclohexanol (24) and 1-cyclohexenemethanol (25). The minor product was the direct displacement product, 5,6-heptadien-1-yl 2,2,2-trifluoroethyl ether (23). The cyclic triflurorethyl ethers were also obtained from the solvolysis of two arenesulfonate esters of 24 and 25, the alcohols having been synthesized by an independent route. Kinetic data showed a rate enhancement for 14 relative to its saturated analog.
|Item Type:||Thesis (Master's thesis)|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Restricted to Caltech community only|
|Defense Date:||19 August 1981|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Tony Diaz|
|Deposited On:||15 Apr 2010 17:40|
|Last Modified:||26 Dec 2012 03:23|
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