Journal of Organic Chemistry p. 429 - 433 (1994)
Update date:2022-08-04
Topics:
Selco, J. I.
Brooks, T.
Chang, M.
Trieu, M. T.
McDonald, J. K.
McManus, S. P.
Photochemical reactivity has been observed in solution-phase azulene.Experiments are described which confirm photoinduced deuteration, chlorination, and polymerization.The threshold for the observed chemistry is at the origin of S2 which is at 27956 +/- 8 cm-1 (357.7 +/- 0.1 nm) in chloroform.Only one photon is required to induce the observed chlorine substitution reactions.Although no naphthalene is formed, this chemical channel appears to be the equivalent of a thermal reaction, with the substitutions taking place at the two equivalent positions on the small ring of azulene.The mechanism of these reactions is bimolecular in nature.Chlorination provides a complex mixture of products in most cases; however, deuteration proceeds cleanly giving only 1,3-d2-azulene.
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