toluene e = 2.37). Calculations were performed using Gaussian03
and Gaussian09 suite of programs,35,36 implemented on dual core
Opteron 240 personal computer under Linux operating system
and computer cluster Isabella at the Computing center of the
University of Zagreb (24 dual processor HP ProLiant BLP20p
nodes with Intel Xeon 2.8 GHz, 32 dual processor Dell 1850 1U
nodes with Intel Xeon 3.4 GHz and 24 dual processor Pyramid
GX28 nodes with AMD Opteron 248). Harmonic vibration
frequencies were calculated for all localized stationary structures
to verify whether they are minima or transition states.
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20 M. Sindler-Kulyk, Z. Stiplosˇek, D. Vojnovic´, B. Metelko and Z.
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21 K. A. Parker and Z. Wang, Org. Lett., 2006, 8, 3553sometimes also
regarded as domino pericyclic reaction: D. Skropeta and R. W.
Rickards, Tetrahedron Lett., 2007, 48, 3281.
22 R. B. Woodward and R. Hoffmann, The Conservation of Orbital
Symmetry, Verlag Chemie, Weinheim, 1970.
23 A. Dahmen and R. Huisgen, Tetrahedron Lett., 1969, 10, 1465.
24 Y. Zhao and D. G. Truhlar, Theor. Chem. Acc., 2008, 120, 215.
25 Y. Zhao and D. G. Truhlar, Acc. Chem. Res., 2008, 41, 157.
26 J. M. Um, H. Xu, K. N. Houk and W. Tang, J. Am. Chem. Soc., 2009,
131, 6664.
ˇ
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27 M. Oliva, L. R. Domingo, V. S. Safont, J. Andre´s, R. Castillo and V.
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Acknowledgements
28 V. A. Pichko, B. Y. Simkin and V. I. Minkin, J. Org. Chem., 1992, 57,
This research was funded by grants from the Croatian ministry of
science, education and sports (125-0982933-2926, 098-0982929-
2917, 098-0982933-3218 and 098-0982933-2920). The computing
center of the Zagreb University is thanked for allocating the time
at the computer cluster Isabella. We would also like to thank Dr
Zoran Glasovac for valuable comments and discussion.
7087.
29 B. E., IV Thomas, J. D. Evanseck and K. N. Houk, J. Am. Chem. Soc.,
1993, 115, 4165.
30 K. N. Houk, Y. Li and J. D. Evanseck, Angew. Chem., Int. Ed. Engl.,
1992, 31, 682.
31 B. Lecea, A. Arrieta and F. P. Cossio, J. Org. Chem., 2005, 70, 1035.
32 C. Hulot, S. Amiri, G. Blond, P. R. Schreiner and J. Suffert, J. Am.
Chem. Soc., 2009, 131, 13387.
33 Thermally forbidden [2 + 2] cyclisation and 6p-electrocyclization as
initial reactions are predicted by M06 calculations to be much higher
in energy (221.2, and 174.4 kJ mol-1, respectively), which rules out the
possibility of these alternative reaction paths.
34 Predictions obtained by the BMK/6-311+G(d,p)//BMK/6-
31G(d)+ZPVE method are essentially identical, while the MP2/6-
311+G(d,p)//MP2/6-31G(d)+ZPVE method, which tends to
underestimate barrier heights for pericyclic reactions (J. B. Thomas,
J. R. Waas, M. Harmata and D. A. Singleton, J. Am. Chem. Soc.,
2008, 130, 14544.) gave incorrect predictions of stereochemical
outcomes.
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