Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations

New Journal of Chemistry

Volumn 28, Issue 5, 2004, Pages 578-584

  Thiemann, Thies ^a   Watanabe, Masataka ^a   Tanaka, Yasuko ^a   Mataka, Shuntaro ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE DERIVATIVE; KETONE; PHOSPHORANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; SOLVENT;

ARTICLE; HEATING; MICROWAVE RADIATION; OLEFINATION; PRIORITY JOURNAL; REACTION TIME; SOLID STATE;

EID: 2942746792     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b311894k     Document Type: Article

References (57)

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22. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
23. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
24. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
25. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
26. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
27. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
28. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
29. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
30. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
31. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
32. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
33. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
34. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
35. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
36. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
37. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
38. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
39. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
40. 13C NMR IR and MS. All new compounds gave correct analytical and/or HR-MS data. A number of compounds have been synthesized previously. M. Hatsuda, T. Kuroda and M. Seki, Synth. Commun., 2003, 33, 427 (3a, 3d); P. Berthelot, C. Vaccher, N. Flouquet, M. Debaert, M. Luyckx and C. Brunet, J. Med. Chem., 1991, 34, 2557 (3b and 3i); K. Okubo, M. Shirai and C. Yokoyama, Tetrahedron Lett., 2002, 43, 7115 (3e); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson and J. Secor, US Pat., 1998, 5780465 (Dow Agrosciences LLC, USA); L. D. Markley, K. E. Arndt, P. G. Ray, T. W. Balko, E. N. K. Cressman, D. G. Ouse, J. L. Jackson, J. Secor, Chem. Abs., 1998, 129, 105503p (3f); J. Masllorens, M. Moreno-Manas, A. Pla-Quintana and A. Roglans, Org. Lett., 2003, 5, 1559 (3g); H. M. Sampath Kumar, M. Sesha Rao, S. Joyasawak and J. S. Yadov, Tetrahedron Lett., 2003, 44, 4287 (3h, 3j, 3o, 3r and 7c); H. J. Bestmann, R. W. Saalfrank and J. P. Snyder, Chem. Ber., 1973, 106, 2601 (3k); C. Dartiguelongue, S. Payan, O. Duval, L. M. Gomes and R. D. Waigh, Bull. Soc. Chim. Fr., 1997, 134, 769 (3m); G. V. Kryshtal, G. M. Zhdankina and S. G. Zlotin, Mendeleev Commun., 2002, 176 (3n); R. B. Moodie, K. Schofield, P. G. Taylor and P. J. Baillie, J. Chem. Soc., Perkin Trans. 2, 1981, 842 (3p); M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron Lett., 1996, 37, 7449 (3s); R. Rossi, A. Carpita, F. Bellina and P. Cossi, J. Organomet. Chem., 1993, 451, 33 (5a); J. A. Soderquist, I. Rosado, Y. Marrero and C. Burgos, ARKIVOC, 2001, 12 (5b); for 7a see ref. 22; for 8a see ref. 21; A. Mayrova-Popivanova and L. Zhelyazkov, Farmatsiya (Sofia), 1988, 38, 1; A. Mayrova-Popivanova and L. Zhelyazkov, Chem. Abs., 1989, 110, 7984x (8c-a/b); A. Katritzky, L. Serdyuk, L. Xie and I. Ghiviriga, J. Org. Chem., 1997, 62, 6215 (8f). 31 and 10 are commercially available.
41. On the average, the proton at C2 (i.e., at the carbon a to the carboxylate function) for the E compound is shifted low-field by Δδ 0.5 when compared to the Z compound. For incremental chemical shift values, see: M. Hesse, H. Meier and B. Zeeh, Spektroskopische Methoden in der organischen Chemie, Thieme Verlag, Stuttgart, 1979, pp. 186 or comparable books on spectroscopic methods.
42. R. F. Hudson and D. A. Chopard, Helv. Chim. Acta, 1963, 46, 2178.
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44. (a) J. I. Cadogan, E. G. Duell and P. W. Inward, J. Chem. Soc. C, 1962, 4164; see also: R. E. Buckles, M. P. Bellis and W. D. Coder, Jr., J. Am. Chem. Soc., 1951, 73, 4972;
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