RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION

MULLER F, Mattay J, STEENKEN S (1993)
The Journal of Organic Chemistry 58(16): 4462-4464.

Journal Article | Published | English

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Abstract
The product of the ring opening of 3-aryl-substituted azirines under conditions of photoinduced electron transfer (PET) is shown to be not a nitrile ylide but a short-lived 2-azaallenyl radical cation. This species has been investigated by pulse radiolysis and gamma-radiolysis techniques. The radical cation has an absorption band with lambda(max) at 485 nm. The lifetime of the radical cation is tau = 1.43 mus in n-butyl chloride. The rate constant for the reaction of the radical cation with the imine 9 is 7.8 X 10(9) M-1 s-1. Gamma-Radiolysis in n-butyl chloride leads to the same products, i.e., an N-alkylated imidazole as in the case of PET.
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MULLER F, Mattay J, STEENKEN S. RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION. The Journal of Organic Chemistry. 1993;58(16):4462-4464.
MULLER, F., Mattay, J., & STEENKEN, S. (1993). RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION. The Journal of Organic Chemistry, 58(16), 4462-4464.
MULLER, F., Mattay, J., and STEENKEN, S. (1993). RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION. The Journal of Organic Chemistry 58, 4462-4464.
MULLER, F., Mattay, J., & STEENKEN, S., 1993. RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION. The Journal of Organic Chemistry, 58(16), p 4462-4464.
F. MULLER, J. Mattay, and S. STEENKEN, “RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION”, The Journal of Organic Chemistry, vol. 58, 1993, pp. 4462-4464.
MULLER, F., Mattay, J., STEENKEN, S.: RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION. The Journal of Organic Chemistry. 58, 4462-4464 (1993).
MULLER, F, Mattay, Jochen, and STEENKEN, S. “RADICAL-CATION [3+2] CYCLOADDITIONS OF 2H-AZIRINES - MECHANISTIC STUDIES CONCERNING THE INTERMEDIATE RADICAL-CATION”. The Journal of Organic Chemistry 58.16 (1993): 4462-4464.
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