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I. Mechanism of the rearrangement of fenchone. II. Mechanism of the Diels-Alder reaction


Lutz, Raymond P. (1962) I. Mechanism of the rearrangement of fenchone. II. Mechanism of the Diels-Alder reaction. Dissertation (Ph.D.), California Institute of Technology.


Part I: The rearrangement of fenchone (1,3,3-trimethylbicyclo[ 2.2.1]-heptan-2-one) to 3,4-dimethylacetophenone has been carried out using a sample labeled with carbon-14 in the methyl groups of the 3-position. In concentrated sulfuric acid at 90°, 96% of the reaction takes the following course: […]

Part II: Optically active methacrolein dimer, labeled with deuterium at the aldehyde hydrogen, rearranges thermally with complete retention of optical activity to the isomer in which the deuterium is shifted to the vinyl position on the ring. The rearrangement is accompanied by […]

substantial competitive formation of methacrolein by a Diels–Alder dissociation, lending support to the presumption that this and analogous isomerizations represent partial reverse Diels-Alder reactions. The results rule out the intervention of a linear intermediate in the Diels-Alder reaction of methacrolein, and make it unlikely that similar intermediates are involved in other Diels-Alder reactions.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Roberts, John D.
Thesis Committee:
  • Unknown, Unknown
Defense Date:1 January 1962
Record Number:CaltechTHESIS:08032011-144903807
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:6572
Deposited By: Tony Diaz
Deposited On:24 Aug 2011 17:11
Last Modified:26 Dec 2012 04:38

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