Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions

Gaebert C, Siegner C, Mattay J, Toubartz M, Steenken S (1998)
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (12): 2735-2740.

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Abstract
The reactive intermediates generated by laser flash photolysis (lambda(exc) = 248 or 193 nm) of the aziridines (E)-1-butyl-2,3-diphenylaziridine 1, (E)-2,3-diphenylaziridine 2, 1,2-dliphenylaziridine 3, 1-(p-methoxyphenyl)-2-phenylaziridine 4 and 1-butyl-2-phenylaziridine 5 in acetonitrile and alcohols as solvents were identified as the corresponding azomethine ylides and spectroscopically and kinetically characterized. The rate constants for the [3 + 2] reaction of the ylides with electron-deficient alkenes to give pyrrolidines are between 10(6) and 10(9) M-1 s(-1). In the case of 1 and 2 iminium ions are produced by protonation (by H2O or ROH) of the ylides (also studied by time-resolved conductance). For this reaction, with MeOH as the proton donor, the kinetic isotope effect is k(MeO-H)/k(MeO-D) = 5-7, from which it is concluded that the transition state for protonation of the carbanionic site of the ylide is linear.
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Gaebert C, Siegner C, Mattay J, Toubartz M, Steenken S. Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2. 1998;(12):2735-2740.
Gaebert, C., Siegner, C., Mattay, J., Toubartz, M., & Steenken, S. (1998). Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(12), 2735-2740.
Gaebert, C., Siegner, C., Mattay, J., Toubartz, M., and Steenken, S. (1998). Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2735-2740.
Gaebert, C., et al., 1998. Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, (12), p 2735-2740.
C. Gaebert, et al., “Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions”, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, pp. 2735-2740.
Gaebert, C., Siegner, C., Mattay, J., Toubartz, M., Steenken, S.: Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2. 2735-2740 (1998).
Gaebert, C, Siegner, C, Mattay, Jochen, Toubartz, M, and Steenken, S. “Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3+2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions”. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 12 (1998): 2735-2740.
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