Kinetics of the 1, 5‐dipolar cyclization of ...



Title Kinetics of the 1, 5‐dipolar cyclization of 2‐Vinylpyridinium ylides to Indolizines. Determination of rate parameters by laser flash photolysis
Author(s) Michael T. H. Liu, Y. N. Romashin, R. Bonneau
Journal International Journal of Chemical Kinetics
Date 1994
Volume 26
Issue 12
Start page 1179
End page 1184
Abstract Nanosecond laser flash photolysis (lambda = 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 mu s at 25 degrees C independent of the concentration of 2-vinylpyridine. As the ylide decays, there isa 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; E(alpha) = 12.1 kcal mol(-1) and log A = 13.4. (C) 1994 John Wiley & Sons, Inc.

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