"In order to investigate the possibility of resonance effects through a non-coplanar substituted acetylene, synthesis of bis-(2,5,8-trimethyl-l-naphthyl)-acetylene was attempted. Condensation of acetylene with 2,5,8-trimethyl-l-tetralone to yield an acetylenic glycol followed by dehydration and dehydrogenation was expected to yield the desired non-coplanar acetylene. Comparison of its ultraviolet spectrum with that of di-l-naphthyl-acetylene would have suggested the true nature of the acetylene pi cloud. The acetylene condensation was unsuccessful, however.
Substituted allenes, which contain one sp hybridized carbon atom, were then successfully synthesized for a similar analysis of potential resonance effects. A series of para-substituted 4-phenyl-2-methylbutadienoic acids were synthesized and their pKa's determined in water solution. The pKa's of the para-methyl, para-chloro and para-hydrogen substituted allenic acids were identical, indicating that resonance effects are not transmitted through the allene function"--Abstract, page iii.
Russell, Robert R.
Wulfman, David S., 1934-2013
Hanna, Samir B.
Webb, William H.
Stoffer, James O.
Ph. D. in Chemistry
University of Missouri at Rolla
vi, 76 pages
© 1967 Robert Andrew Steinkamp, All rights reserved.
Dissertation - Open Access
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Steinkamp, Robert Andrew, "Study of resonance effects in allenic and related systems" (1967). Doctoral Dissertations. 429.