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Thesis (M.S.)—University of Nebraska—Lincoln, 1958. Department of Chemistry.


Copyright 1958, the author. Used by permission.


The objectives of this problem were threefold: (1) to prepare a number of spiroepoxy ketones of the 2-benzal-1-tetralone series; (2), to study the reactions of these ketones with amines and other bases, and to study their behavior in acidic media; (3), to obtain absorption spectra of pertinent compounds and to relate this information to the molecular structure of the compounds.

The parent oxide of this investigation, 2-benzal-1-tetralone oxide, was subjected to various reaction conditions and found to be very susceptible to degradation.The possibility of abnormal ring opening has been offered as the cause of this situation.

The preparation of new benzal-substituted derivatives of 2-benzal-1-tetralone was accomplished.Four new spiroepoxy ketones of the 2-benzal-1-tetralone oxide series was synthesized.The ultraviolet and infrared absorption spectra of the above mentioned new compounds were obtained and related to structural proof.Assignment of infrared spectral bands for individual vibrating groups were made.

Advisor:N. H. Cromwell