Abstract
Electrospray ionization mass spectrometry was used to study chemical electron-transfer reactions of 1,2-diarylcyclopropanes by Cu(II) salt in acetonitrile. The ion [M − H]+ with a hydrogen atom loss and the solvent adduct ions, [M+42]+, etc., were detected as the initial reaction products, where [M+42]+ represents the ion whose mass is 42 u greater than the parent molecule M. From the study of deuterated derivatives, the hydrogen abstraction was revealed to occur at the 3 position of the cyclopropanes, and the mechanism of the hydrogen abstraction reaction and of the solvent addition were discussed.
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Mizuno, K.; Ichinose, N.; Otsuji, Y. J. Org. Chem. 1992, 57, 1855–1860.
Mizuno, K.; Ichinose, N.; Otsuji, Y. Chem. Lett. 1988, 433–436.
Miyashi, T.; Kamata, M.; Mukai, T. J. Am. Chem. Soc. 1987, 109, 2780–2788.
Yamashita, M.; Fenn, J. B. J. Phy. Chem. 1984, 88, 4451–4559; 1984, 88, 4671–4675.
Whitehouse, C. M.; Dreyer, R. N.; Yamashita, M.; Fenn, J. B. Anal. Chem. 1985, 57, 675–679.
Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. K.; Whitehouse, C. M. Science 1989, 246, 64–71.
Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. K. Mass Spectrom. Rev. 1990, 9, 37–70.
Smith, R. D.; Loo, J. A.; Edmonds, C. G.; Barinaga, C. J.; Udeth, H. R. Anal. Chem. 1990, 62, 882–889.
Mann, M. Org. Mass Spectrom. 1990, 25, 575–587.
Katta, V.; Chowdhury, S. K.; Chait, B. T. J. Am. Chem. Soc. 1990, 112, 5348–5349.
Van Berkel, G. J.; McLuckey, S. A.; Glish, G. L. Anal. Chem. 1991, 63, 1098–1109.
Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250–5256.
Que, L.; Jr. Jinheung, K.; Yanhong, D.; Edmund, L. Inorg. Chem. 1996, 35, 2369–2372.
Arakawa, R.; Lu, J.; Inoue, H.; Doe, H.; Matsuo, T. Int. J. Mass Spectrom. Ion Processes 1997, 160, 371–376.
Van Berkel, G. J.; Zhou, F. Anal. Chem. 1994, 66, 3408–3415.
Van Berkel, G. J.; Asano, K. G.; McLuckey, S. A. J. Am. Soc. Mass. Spectrom. 1994, 5, 689–692.
Van Berkel, G. J.; Asano, K. G. Anal. Chem. 1994, 66, 2096–2102.
Zhou, F.; Van Berkel, G. J.; Donovan, B. T. J. Am. Chem. Soc. 1994, 116, 5485–5486.
Xu, X.; Nolan, S. P.; Cole, R. B. Anal. Chem. 1994, 66, 119–125.
Ritter, J. J.; Kalish, J. Org. Synth. 1973, 53, 471–473.
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Okamoto, M., Doe, H., Mizuno, K. et al. Electrospray mass analysis of chemical oxidation of 1,2-diarylcyclopropanes by Cu(II) salt. J Am Soc Mass Spectrom 9, 966–969 (1998). https://doi.org/10.1016/S1044-0305(98)00064-6
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DOI: https://doi.org/10.1016/S1044-0305(98)00064-6