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Methylenecyclobutene and Related Substances


Applequist, Douglas Einar (1955) Methylenecyclobutene and Related Substances. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/7N2P-TH64.


Methylenecyclobutene was synthesized by a modification of the Willstatter cyclobutene synthesis, with the use of the Hofmann reaction to introduce the intracyclic double bond. A novel feature of the synthesis was the use of anthracene as a blocking group for the exocyclic double bond during the malonic-ester ring closure. 4,4-Dimethylmethylenecyclobutene was synthesized from pinene, and 3-phenylmethylenecyclobutene was obtained by condensation of allene and phenylacetylene. The structures of the methylenecyclobutene dibromides and of the polymers formed by three different mechanisms were investigated. The results were shown to be consistent with the predictions of simple molecular orbital theory. 3-Methylenetrimethylene oxide was synthesized and its structure investigated by electron diffraction. The structures of the dibromides of methylenecyclobutane were determined and found to be consistent with a carbonium-ion mechanism for bromine addition.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:(Chemistry and Biology)
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Minor Option:Biology
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Roberts, John D.
Thesis Committee:
  • Unknown, Unknown
Defense Date:1 January 1955
Record Number:CaltechETD:etd-11202003-141714
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:4606
Deposited By: Imported from ETD-db
Deposited On:21 Nov 2003
Last Modified:28 Jun 2023 17:23

Thesis Files

PDF (Applequist_de_1955.pdf) - Final Version
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