International Journal of Chemical Kinetics p. 1179 - 1184 (1994)
Update date:2022-08-17
Topics:
Liu, Michael T. H.
Romashin, Yuri N.
Bonneau, Roland
Nanosecond laser flash photolysis (λ = 355 nm) of an aqueous solution of 3-chloro-3-p-chlorophenyldiazirine in isooctane produces a transient absorption at 310 nm due to the formation of the carbene. In the presence of 2-vinylpyridine, a second transient with a broad absorption band peaking at 520 nm grows in. This absorption is attributed to 2-vinylpyridinium ylide. The ylide decays with a lifetime equal to 33 μs at 25 deg C independent of the concentration of 2-vinylpyridine. As the ylide decays, there is a concomitant growth of an absorption at 330 nm, attributed to the formation of indolizine. The activation parameters for the 1,5-dipolar cyclization of the ylide to indolizine were determined; Ea = 12.1 kcal mol-1 and log A = 13.4.
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