The Journal of Organic Chemistry
Article
temperature controller. For irradiations, a mercury high-pressure lamp
(HBO 200) with a monochromator was used (bandwidth ca. 10 nm).
IR spectra were recorded with an FTIR spectrometer (4500−
300 cm−1, resolution 0.7 cm−1), while UV/vis spectra were recorded
with a UV/vis spectrophotometer. For matrix isolation of oxadiazoline
4a, the compound was sublimed at −5 °C and co-condensed with a
high excess of argon on the surface of a CsI (BaF2) window at 10 K.
The obtained matrices were photolyzed, and the formed products
were analyzed by means of FT-IR and UV/vis spectroscopy.
For the combination of VFP with matrix isolation, a home-built,
water-cooled oven directly connected to the vacuum shroud of the
cryostat was employed. The pyrolysis zone consisted of an empty
quartz tube (inner diameter 8 mm, length of heating zone 50 mm)
resistively heated by a thermo-coax wire. The temperature was
controlled by a Ni/CrNi thermocouple.
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ASSOCIATED CONTENT
* Supporting Information
■
S
NMR spectra of all new compounds and crystallographic data
of 6 (CIF); computational results (structures, Cartesian
coordinates, energies) for 1a,b, 8−10, 1-TS, 8-TS, 9-TS, and
10-TS at the MP2/6-311+G(d,p) and B3LYP/6-311+G(d,p)
levels of theory. This material is available free of charge via the
(9) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457.
̌
(10) (a) Su, K.-J.; Pacar, M.; Mieusset, J.-L.; Arion, V. B.; Brinker, U.
H. J. Org. Chem. 2011, 76, 4971. (b) Mieusset, J.-L; Schrems, A.;
Abraham, M.; Arion, V. B.; Brinker, U. H. Tetrahedron 2009, 65, 765.
(c) Mieusset, J.-L; Abraham, M.; Brinker, U. H. J. Am. Chem. Soc.
2008, 130, 14634. (d) Mieusset, J.-L; Billing, P; Abraham, M.; Arion,
V. B.; Brecker, L.; Brinker, U. H. Eur. J. Org. Chem. 2008, 5336.
(e) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2007, 72, 263.
(f) Mieusset, J.-L; Brinker, U. H. J. Am. Chem. Soc. 2006, 128, 15843.
(g) Freeman, P. K.; Pugh, J. K. J. Org. Chem. 2000, 65, 6107.
(h) Freeman, P. K. J. Am. Chem. Soc. 1998, 120, 1619. (i) Fleischhauer,
AUTHOR INFORMATION
Corresponding Author
Notes
■
I.; Brinker, U. H. Chem. Ber. 1987, 120, 501. (j) Brinker, U. H.; Konig,
̈
The authors declare no competing financial interest.
L. Chem. Lett. 1984, 45. (k) Brinker, U. H.; Konig, L. Chem. Ber. 1983,
̈
116, 894. (l) Kirmse, W.; Chiem, P. V.; Henning, P. G. J. Am. Chem.
ACKNOWLEDGMENTS
■
Soc. 1983, 105, 1695. (m) Brinker, U. H.; Konig, L. J. Am. Chem. Soc.
̈
We thank Prof. Dr. Vladimir B. Arion, Institute of Inorganic
Chemistry, University of Vienna, for determining the structure
of oxadiazoline 6 by single-crystal X-ray analysis and Dozent
Dr. Lothar Brecker, Institute of Organic Chemistry, University
of Vienna, for his help with the assignment of NMR spectra
presented herein.26
1981, 103, 212. (n) Brinker, U. H.; Ritzer, J. J. Am. Chem. Soc. 1981,
103, 2116. (o) Brown, W. T.; Jones, W. M. J. Org. Chem. 1979, 44,
3090. (p) Neff, J. R.; Nordlander, J. E. J. Org. Chem. 1976, 41, 2590.
(11) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci,
B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.
P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.;
Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima,
T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; ,
J.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.;
Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.;
Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.;
Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.;
Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.;
Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.;
Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador,
P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.;
Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, rev.
B.01 ed.; Gaussian, Inc.: Wallingford, 2010.
DEDICATION
■
Dedicated to Prof. Dr. Gunther Maier on the occasion of his
̈
80th birthday.
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