Synthesis of poly-ferrocene heterocycles by cycloaddition of mono- or bis(ferrocenecarbonyl)acetylenes and bis[1,2]dithiolo[1,4]thiazinethiones

Tetrahedron

Volumn 58, Issue 49, 2002, Pages 9785-9792

  Barriga, Susana ^a   Marcos, Carlos F ^b   Riant, Olivier ^c   Torroba, Tomás ^a  

^a UNIVERSITY OF BURGOS   (Spain)

^b UNIVERSITY OF EXTREMADURA   (Spain)

^c UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Cyclic voltammetry; Dithiole; Extended TTF; Ferrocene; Heterocycle; Thiazine

Indexed keywords

3,5 BIS(BISFERROCENECARBONYL 1,3 DITHIOLYLIDENE)[1,4]THIAZINE; ACETYLENE DERIVATIVE; BISFERROCENYLBUTYNEDIONE; BIS[1,2]DITHIOLO[1,4]THIAZINE KETOTHIONE; FERROCENE DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE; TETRATHIAFULVALENE DERIVATIVE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037010821     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01295-4     Document Type: Article

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28. Recent examples are: (a) Caramo M., Curad T., Deschenaux R., Even M., Marcaccio M., Paolucci F., Prato M., Bofia S. J. Mater. Chem. 12:2002;829-833 (b) Even M., Heinrich B., Guillon D., Guldi D.M., Prato M., Deschenaux R. Chem. Eur. J. 7:2001;2595-2604 (c) Seo J.S., Yoo Y.S., Choi M.G. J. Mater. Chem. 11:2001;1332-1338 (d) Nakamura N., Maekawahara H., Hanasaki T., Yamaguchi T. Mol. Cryst. Liq. Cryst. 352:2000;559-566 (e) Deschenaux R., Schweissguth M., Vilches M.T., Levelut A.M., Hautot D., Long G.J., Luneau D. Organometallics. 18:1999;5553-5559. (f) For a review, see: Imrie C., Engelbrecht P., Loubser C., McCleland C.W. Appl. Organomet. Chem. 15:2001;1-15.
29. Recent examples are: (a) Caramo M., Curad T., Deschenaux R., Even M., Marcaccio M., Paolucci F., Prato M., Bofia S. J. Mater. Chem. 12:2002;829-833 (b) Even M., Heinrich B., Guillon D., Guldi D.M., Prato M., Deschenaux R. Chem. Eur. J. 7:2001;2595-2604 (c) Seo J.S., Yoo Y.S., Choi M.G. J. Mater. Chem. 11:2001;1332-1338 (d) Nakamura N., Maekawahara H., Hanasaki T., Yamaguchi T. Mol. Cryst. Liq. Cryst. 352:2000;559-566 (e) Deschenaux R., Schweissguth M., Vilches M.T., Levelut A.M., Hautot D., Long G.J., Luneau D. Organometallics. 18:1999;5553-5559. (f) For a review, see: Imrie C., Engelbrecht P., Loubser C., McCleland C.W. Appl. Organomet. Chem. 15:2001;1-15.
30. Recent examples are: (a) Caramo M., Curad T., Deschenaux R., Even M., Marcaccio M., Paolucci F., Prato M., Bofia S. J. Mater. Chem. 12:2002;829-833 (b) Even M., Heinrich B., Guillon D., Guldi D.M., Prato M., Deschenaux R. Chem. Eur. J. 7:2001;2595-2604 (c) Seo J.S., Yoo Y.S., Choi M.G. J. Mater. Chem. 11:2001;1332-1338 (d) Nakamura N., Maekawahara H., Hanasaki T., Yamaguchi T. Mol. Cryst. Liq. Cryst. 352:2000;559-566 (e) Deschenaux R., Schweissguth M., Vilches M.T., Levelut A.M., Hautot D., Long G.J., Luneau D. Organometallics. 18:1999;5553-5559. (f) For a review, see: Imrie C., Engelbrecht P., Loubser C., McCleland C.W. Appl. Organomet. Chem. 15:2001;1-15.
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36. Recent examples are: (a) Nemykin V.N., Kobayashi N. Chem. Commun. 2001;165-166 (b) Stankovic E., Toma S., Van Boxel R., Asselberghs I., Persoons A. J. Organomet. Chem. 637-639:2001;426-434 (c) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671-2687.
37. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
38. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
39. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
40. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
41. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
42. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
43. Recent examples are: (a) Fukuzumi S., Okamoto K., Imahori H. Angew. Chem. Int. Ed. Engl. 41:2002;620-622 (b) Gan J., Tian H., Wang Z.H., Chen K.H., Hill J., Lane P.A., Rahn M.D., Fox A.M., Bradley D.D.C. J. Organomet. Chem. 645:2002;168-175 (c) Plenio H., Aberle C. Chem. Eur. J. 7:2001;4438-4446 (d) Plenio H., Aberle C., Al Shihadeh Y., Lloris J.M., Martinez-Manez R., Pardo T., Soto J. Chem. Eur. J. 7:2001;2848-2861 (e) Imahori H., Guldi D.M., Tamaki K., Yoshida Y., Luo C.P., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;6617-6628 (f) Imahori H., Tamaki K., Guldi D.M., Luo C.P., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S. J. Am. Chem. Soc. 123:2001;2607-2617. For a review, see: (g) Kaifer A.E. Acc. Chem. Res. 32:1999;62-71.
44. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
45. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
46. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
47. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
48. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
49. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
50. Recent examples are: (a) Stone D.L., Smith D.K., McGrail P.T. J. Am. Chem. Soc. 124:2002;856-864 (b) Palomero J., Mata J.A., González F., Peris E. New J. Chem. 26:2002;291-297 (c) Ashton P.R., Balzani V., Clemente-León M., Colonna B., Credi A., Jayaraman N., Raymo F.M., Stoddart J.F., Venturi M. Chem. Eur. J. 8:2002;673-684 (d) Kim C., Park E., Song C.K., Koo B.W. Synth. Met. 123:2001;493-496 (e) Sengupta S., Sadhukhan S.K. Organometallics. 20:2001;1889-1891 (f) Nlate S., Ruiz J., Blais J.C., Astruc D. Chem. Commun. 2000;417-418. For a review, see: (g) Cardona C.M., Mendoza S., Kaifer A.E. Chem. Soc. Rev. 29:2000;37-42.
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