A. Masuyama et al. / Tetrahedron 59 (2003) 353–366
365
3. Nonami, Y.; Baran, J.; Sosnicki, J.; Mayr, H.; Masuyama, A.;
Nojima, M. J. Org. Chem. 1999, 64, 4060.
plots and tables were carried out using the SHELXTL PC
suite of programs.22
4. (a) Dussault, P. H. Active Oxygen in Chemistry; Foote, C. S.,
Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie:
London, 1995; Vol. 2, pp 141–203, Chapter 5.
(b) McCullough, K. J.; Motomura, Y.; Masuyama, A.; Nojima,
M. Chem. Commun. 1998, 1173 and references therein.
5. (a) Wasserman, H. H.; Murray, R. W. Singlet Oxygen;
Academic: New York, 1979; Chapter 8, pp 287–427.
(b) Frimer, A. A. Chem. Rev. 1979, 79, 359. (c) Foote, C. S.;
Clennan, E. L. Active Oxygen in Chemistry; Foote, C. S.,
Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie:
London, 1995; Vol. 2, pp 116–117, Chapter 4. (d) Stratakis,
M.; Orfanopoulos, M. Tetrahedron 2000, 56, 1595.
6. Porter, N. A. In Organic Peroxides; Ando, W., Ed.; Wiley:
New York, 1992; pp 107–111, Chapter 2.
Crystal data for dimer 38. C16H26O2, M¼250.37, colorless
needles, monoclinic, space group C2/c (No. 15),
˚
˚
˚
a¼15.4720(10) A, b¼6.0750(10) A, c¼14.2700(10) A,
3
23
˚
b¼93.690(10)8, U¼1338.5(3) A , Z¼4, Dc¼1.242 g cm
,
F(000)¼552, m(Mo Ka)¼0.079 mm21, final discrepancy
factors: R1¼0.035 and wR 2¼0.087.
Crystal data for compound 53b. C13H23ClO, M¼230.77,
colorless needles, triclinic, space group P-1 (No. 2),
˚
˚
˚
a¼10.902(2) A, b¼10.904(2) A, c¼23.210(3) A, a¼
80.290(10)8, b¼80.76(2)8, g¼89.890(10)8, U¼
2683.4(8) A , Z¼8, Dc¼1.142 g cm23, F(000)¼1008,
3
˚
m(Mo Ka)¼0.261 mm21
,
final discrepancy factors:
R1¼0.056 and wR 2¼0.132.
7. (a) Bartlett, P. D.; Mendenhall, G. D. J. Am. Chem. Soc. 1970,
92, 210. (b) Kopecky, K. R.; Scott, W. A.; Lockwood, P. A.;
Mumford, C. Can. J. Chem. 1978, 56, 1114. (c) Mori, A.; Abe,
M.; Nojima, M. J. Org. Chem. 2001, 66, 3548 and references
therein.
Crystallographic data (excluding structure factors) for
structures of 38 and 53b have been deposited with the
Cambridge Crystallographic Data Centre as supplementary
publication numbers CCDC 191224 and 191225. Copies of
the data can be obtained free of charge on application to
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax:
þ44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
8. Giese, B. Radicals in Organic Synthesis: Formation of
Carbon–Carbon Bonds; Pergamon: Oxford, 1986; Chapter 2.
9. (a) Galatsis, P.; Scott, D. M.; Faber, T. J. Org. Chem. 1993, 58,
1215. (b) Afzal, M.; Walton, J. C. J. Chem. Soc., Perkin Trans.
2 1999, 937.
10. (a) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59,
3186. (b) Molander, G. A. Acc. Chem. Res. 1998, 31, 603.
(c) Jung, M. E. Synlett 1999, 843.
Acknowledgements
11. Beckwith, A. L. J.; Zimmermann, J. J. Org. Chem. 1991, 56,
5791–5796.
This work was supported in part by a Grant-in-Aid for
Scientific Research (13650904, 14021066 and 14550809)
from the Ministry of Education, Culture, Sports, Science
and Technology.
12. Galli, C.; Giovannelli, G.; Illuminati, G.; Mandolini, L. J. Org.
Chem. 1979, 44, 1258.
13. (a) Beckwith, A. L. J.; Drok, K.; Maillard, B.; Degueil-
Castaing, M.; Philippon, A. Chem. Commun. 1997, 499.
(b) Philippon, A.; Degueil-Castaing, M.; Beckwith, A. L. J.;
Maillard, B. J. Org. Chem. 1998, 63, 6814.
14. Willmore, N. D.; Goodman, R.; Lee, H.-H.; Kennedy, R. M.
J. Org. Chem. 1992, 57, 1216.
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