Liu, Michael T. H., et al. “Kinetics of the 1, 5‐dipolar Cyclization of 2‐Vinylpyridinium Ylides to Indolizines. Determination of Rate Parameters by Laser Flash Photolysis”. International Journal of Chemical Kinetics, vol. 26, no. 12, 1994, pp. 1179-84, https://scholar2.islandarchives.ca/islandora/object/ir%3Air-batch6-1391.

Genre

  • Journal Article
Contributors
Author: Liu, Michael T. H.
Author: Bonneau, R.
Author: Romashin, Y. N.
Date Issued
1994
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.

Note

UNIV BORDEAUX 1,CHIM PHYS LAB,CNRS,URA 348,F-33405 TALENCE,FRANCE.; LIU, MTH, UNIV PRINCE EDWARD ISL,DEPT CHEM,CHARLOTTETOWN C1A 4P3,PE,CANADA.

NEW YORK; 605 THIRD AVE, NEW YORK, NY 10158-0012

JOHN WILEY & SONS INC

PT: J; CR: BONNEAU R, 1989, J CHEM SOC P1, P1547 BONNEAU R, 1994, J CHEM SOC CHEM COMM, P509 DIX EJ, 1993, J AM CHEM SOC, V115, P10424 FLITSCH W, 1984, COMPREHENSIVE HETERO, V4, P443 GRAHAM WH, 1965, J AM CHEM SOC, V87, P4396 KATRITZKY AR, 1990, ADV HETEROCYCLIC CHE, V47, P216 LIU MTH, IN PRESS J PHOTO CHE LIU MTH, 1994, RES CHEM INTERMEDIAT, V20, P195 MODARELLI DA, 1992, J AM CHEM SOC, V114, P7304 UCHIDA T, 1976, SYNTHESIS-STUTTGART, P209; NR: 10; TC: 13; J9: INT J CHEM KINET; PG: 6; GA: PR800

Source type: Electronic(1)

Language

  • English

Subjects

  • Chemistry, Physical
Page range
1179-1184
Host Title
International Journal of Chemical Kinetics
Host Abbreviated Title
Int J Chem Kinet
Volume
26
Issue
12
ISSN
0538-8066

Department