The Journal of Organic Chemistry
ARTICLE
suction to yield 15N-substituted 1 (0.22 g, 0.8 mmol, 93% yield). H
NMR (CDCl3, 400 MHz): δ 2.63 (s, 3H), 5.80 (s, 1H), 7.54 (d, J = 8 Hz,
2H), 8.02 (d, J = 8 Hz, 2H) ppm. 13C NMR (CDCl3, 100 MHz): δ 26.7,
78.1, 78.2, 126.7, 129.0, 138.1, 139.2, 197.3 ppm. 15N NMR (CDCl3, 75
MHz), external standard (H2NC(O)NH2): δ 93.1, 227.5, 262.1 ppm. IR
(CDCl3): 3281, 3060, 3006, 2923, 2345, 2087 (s, N3), 1687 (s, CdO),
1610, 1577, 1508, 1412, 1359, 1338, 1304, 1290, 1266, 1239, 1179, 1115,
1075, 1017, 959, 895, 813, 764, 739, 712, 658, 637, 616, 596, 555, 500,
477 cmÀ1. HRMS: m/z calculated for C9H9O14N415N2 [M + H]+,
219.0779; found, 219.0768.
support from the University Research Council at the University
of Cincinnati and for a Harry B. Mark fellowship.
1
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’ ASSOCIATED CONTENT
S
Supporting Information. Cartesian coordinates, energies,
b
and vibrational frequencies of 1À8 and NMR spectra of 1, 1-d5,
1-15N, 2, and 3. This material is available free of charge via the
’ AUTHOR INFORMATION
Corresponding Author
*E-mail: anna.gudmundsdottir@uc.edu.
’ ACKNOWLEDGMENT
This work was supported by the National Science Foundation
and the Ohio Supercomputer Center. R.A.A.U.R. is grateful for
8187
dx.doi.org/10.1021/jo201304c |J. Org. Chem. 2011, 76, 8177–8188