Abstract
THE elegant brominating reagent, N-bromo-succinimide, has been employed by Karrer1 to prepare fcisdehydrolycopene from the acyclic carot-enoid, lycopene. It has now been shown that the cyclic compound β-ionone reacts in a facile manner with this reagent, giving a bromo-derivative which on dehydrobromination with diethylaniline yields dehydro-β-ionone (I), b.p. 75° at 1 mm. mercury pressure, n22D 1.5497. The absorption spectrum exhibited maxima at 2210 A. and 3380 A. (ε = 7,000 and 9,000 respectively). The product was characterized by the formation of a semicarbazone (m.p. 144–146°) and a 2 : 4-dinitrophenylhydrazone (m.p. 150–151°).
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References
Karrer, P., and Rutschmann, J., Helv. Chim. Ada, 26, 793 (1945).
Gray, E. LeB., and Cawley, J. D., J. Biol. Chem., 134, 397 (1940).
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HENBEST, H. Synthesis of Dehydro-β-lonone. Nature 161, 481 (1948). https://doi.org/10.1038/161481a0
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DOI: https://doi.org/10.1038/161481a0
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