Cycloaddition of phosphoniumꢀiodonium ylides
Russ.Chem.Bull., Int.Ed., Vol. 57, No. 10, October, 2008
2239
The residue was chromatographed on a column using benzene,
dichloromethane, and then a CH2Cl2/MeOH mixture in a graꢀ
dient from 100 : 1 to 20 : 1 as the eluents. The yield of compound
3. A. Herrera, R. MartinezꢀAlvarez, P. Ramiro, D. Molero,
J. Almy, J. Org. Chem., 2006, 71, 3026.
4. Sh. Sano, H. Shimizu, Kw. Kim, W. S Lee, M. Shiro,
Y. Nagao, Chem. Pharm. Bull., 2006, 54, 196.
5. Q. Wang, Br. Ganem, Tetrahedron Lett., 2003, 44, 6829.
6. Ch. Batsila, G. Kostakis, L. P. Hadjiarapoglou, Tetrahedron
Lett., 2002, 43, 5997.
7. E. P. Gogonas, L. P. Hadjiarapoglou, Tetrahedron Lett.,
2000, 41, 9299.
8. E. D. Matveeva, T. A. Podrugina, Yu. K. Grishin, V. V.
Tkachev, V. V. Zhdankin, S. M. Aldoshin, N. S. Zefirov, Zh.
Org. Khim., 2003, 39, 572 [J. Org. Chem., 2003, 39 (Engl.
Transl.)].
1
3 was 0.05 g (30%). H NMR (CDCl3), δ: 0.99 (t, 3 H, CH3,
J = 7.1 Hz); 2.49 (s, 3 H, CH3), 4.32 (q, 2 H, CH2, J = 7.1 Hz);
7.65—7.80 (m, 15 H, arom.). 13C NMR (CDCl3), δ: 14.15 (s,
CH3); 14.22 (s, CH3); 70.63 (s, OCH2); 118.21 (d, Cipso arom.,
1JC,P = 95.3 Hz), 130.19 (d, Cm arom., 3JC,P = 13.9 Hz), 134.19
2
(d, Co arom., JC,P = 11.0 Hz), 135.21 (s, Cp arom.), 155.47
(s, C—O), 167.01 (s, C—CH3). 31P NMR (CDCl3), δ: 8.64.
IR, ν/cm–1: 1590, 1630 (ring), 1730 (C=O). Found (%): C,
59.86; H, 4.82; N, 3.08. C24H23BF4NO2P. Calculated (%):
C, 60.63; H, 4.84; N, 2.95.
9. E. D. Matveeva, T. A. Podrugina, Yu. K. Grishin, A. S.
Pavlova, N. S. Zefirov, Zh. Org. Khim., 2007, 43, 209 [J. Org.
Chem., 2007, 43 (Engl. Transl.)].
10. E. D. Matveeva, T. A. Podrugina, A. S. Pavlova, A. V.
Mironov, N. S. Zefirov, Izv. Akad. Nauk, Ser. Khim., 2008,
391 [Russ. Chem. Bull., Int. Ed., 2008, 57, 400].
11. M. C. Burla, M. Camalli, B. Carrozzini, G. Cascarano,
C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr.,
2003, 36, 1103.
This study was financially supported by the Russian
Foundation for Basic Research (Project No. 05ꢀ03ꢀ33054),
the Council on Grants of the President of the Russian
Federation (Program for State Support of Leading Scienꢀ
tific Schools, Grant NShꢀ2552.2006.3), the Ministry of
Education and Science of the Russian Federation (Target
Program “Development of the Research Potential of Higher
Education,” Grant RNP.2.1.1.7779), and the Division of
Chemistry and Materials Science of the Russian Academy
of Sciences (Program No. 1 for Basic Research).
12. V. Petricek, M. Dusek, L. Palatinus, Jana2000, Structure
Determination Software Programs, Institute of Physics, Praha,
Czech Republic, 2000.
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in revised form June 20, 2008