Dynamics for reaction of an ion pair in aqueous solution: Reactivity of carboxylate anions in bimolecular carbocation-nucleophile addition and unimolecular ion pair collapse

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1237-1240

  Tsuji, Yutaka ^a   Mori, Tetsuo ^a   Richard, John P ^b   Amyes, Tina L ^b   Fujio, Mizue ^c   Tsuno, Yuho ^c  

^a KURUME NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^b UNIVERSITY AT BUFFALO   (United States)

^c KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBON; ESTER; ION; POLITEF;

ARTICLE; CHEMISTRY; KINETICS; METHODOLOGY; ORGANIC CHEMISTRY;

ANIONS; CARBON; CHEMISTRY, ORGANIC; ESTERS; IONS; KINETICS; POLYTETRAFLUOROETHYLENE;

EID: 0035912317     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015706s     Document Type: Article

References (23)

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11. 2 (99% enrichment, Aldrich). The reaction was quenched with 10% HCl (200 mL), the product was extracted into ether, and the ethereal layer was washed with saturated brine. The acid was extracted into 10% NaOH which was then carefully neutralized with concentrated HCl. The product was collected by filtration, dried in vacuo, and used without further purification (58% yield).
12. Rubottom, G. M.; Kim, C.-W. J. Org. Chem. 1983, 48, 1550-1552.
13. 13COMe (64% yield).
14. 4, and evaporated to give the oxygen-18 enriched alcohol which was esterified without further purification.
15. CH = 150 Hz).
16. 13C NMR spectra were recorded on a JNM-A500 FT NMR spectrometer operating at 126 MHz. Spectra used to determine the oxygen-18 enrichment at the bridging and nonbridging positions of the ester were acquired using a sweep width of 250 Hz, 8192 data points (0.03 Hz/pt), and an 8 s relaxation delay.
17. 13C NMR.
18. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161-169. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345-375. Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209-219.
19. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161-169. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345-375. Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209-219.
20. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161-169. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345-375. Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209-219.
21. 1f These data provide a qualitative description of the partitioning of the ion pair intermediates of these reactions but not the absolute rate constant for ion pair return reported here.
22. 2b
23. McClelland, R. A.; Kanagasabapathy, V. M.; Banait, N. S.; Steenken, S. J. Am. Chem. Soc. 1991, 113, 1009-1014.