m-benzyne reacts as an electrophile [3]

Journal of the American Chemical Society

Volumn 122, Issue 36, 2000, Pages 8781-8782

  Nelson, Eric D ^a   Artau, Alexander ^a   Price, Jason M ^a   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIDEHYDROBENZENE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL STRUCTURE; DISSOCIATION; IRRADIATION; ISOMERISM; LETTER; MASS SPECTROMETRY;

EID: 0034644418     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001837x     Document Type: Letter

References (18)

1. Sander, W. Acc. Chem. Res. 1999, 32, 669-676.
2. Hu, J.; Squires, R. R. J. Am. Chem. Soc. 1996, 118, 5816-5817.
3. Thoen, K. K.; Kenttämaa, H. I. J. Am. Chem. Soc. 1999, 121, 800-805.
4. Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896-4903.
5. Roth, W. R.; Hopf, H.; Wasser, T. Zimmermann, H.; Werner, C. Liebigs Ann. 1996, 1691-1695.
6. Logan, C. F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113-2114.
7. Wenthold, P. G.; Squires, R. R.; Lineberger, W. C. J. Am. Chem. Soc. 1998, 120, 5279-5290.
8. Ion 1 was generated by collision-activated dissociation (CAD) of the 3,5-dinitrobenzoyl cation produced by 20 eV electron ionization of 3,5-dinitrobenzoyl chloride in an FT-ICR mass spectrometer. Experiments were conducted as described in ref 3.
9. Nelson, E. D.; Kenttämaa, H. I. Submitted for publication.
10. Schleyer, P. V.; Jiao, H. J.; Glukhovtsev, M. N.; Chandrasekhar, J.; Kraka, E. J. Am. Chem. Soc. 1994, 116, 10129-10134.
11. These ions were generated using the method of ref 3.
12. Marinelli, P. J.; Paulino, J. A.; Sunderlin, L. S.; Wenthold, P. G.; Poutsma, J. C.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1994, 130, 89-105.
13. Rodgers, M. T.; Ervin, K. M.; Armentrout, P. B. J. Chem. Phys. 1997, 106, 4499-4508.
14. Ion 7 was generated in the flowing afterglow-triple quadrupole apparatus by electron ionization of 3,5-dinitrobenzoyl chloride to form the 3,5-didehydrophenyl cation (see ref 9 for more discussion of this ion and its reactivity). Reaction of this species with 4-tert-butylpyridine forms the N-(3,5-dehydrophenyl)-4-tert-butylpyridinium ion which reacts further to form the bis(4-tert-butylpyridinium)phenide cation.
15. (a) Bierbaum, V. M.; DePuy, C. H.; Shapiro, R. H. J. Am. Chem. Soc. 1977, 99, 5800-5802.
16. (b) Hill, B. T.; Poutsma, J. C.; Chyall, L. J.; Hu, J.; Squires, R. R. J. Am. Soc. Mass Spectrom. 1999, 10, 896-906.
17. Kim, S. S.; Yang, K. W.; Lee, C. S. J. Org. Chem. 1996, 61, 4827-4829.
18. Lias, S. G. Ionization Energy Evaluation. In NIST Chemistry WebBook; NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; March 1998; National Institute of Standards and Technology: Gaithersburg MD, 20899 (http://webbook.nist.gov).