Ethynyl[2.2]paracyclophanes and 4-isocyano[2.2]paracyclophane as ligands in organometallic chemistry

Journal of Organometallic Chemistry

Volumn 692, Issue 4, 2007, Pages 839-850

  Clément, Sébastien ^a   Guyard, Laurent ^a   Knorr, Michael ^a   Dilsky, Stefan ^b   Strohmann, Carsten ^b   Arroyo, Marta ^c  

^a UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

2.2 Paracyclophanes; Alkyne; Bis silylation; Cobalt; Iron; Isocyanide; Platinum

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COBALT; COMPLEXATION; IRON; ORGANIC POLYMERS; PLATINUM; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

ALKYNE; BIS-SILYLATION; CONJUGATED SYSTEM; COREY-FUCHS REACTION; PARACYCLOPHANE;

ORGANOMETALLICS;

EID: 33845881433     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.10.039     Document Type: Article

References (107)

1. Brown C.J., and Farthing A.C. Nature 164 (1949) 915
2. Cram D.J., and Steinberg H. J. Am. Chem. Soc. 73 (1951) 5691
3. Bräse S., and Dahmen S. Chem. Commun. (2002) 26
4. Kreis M., Nieger M., and Bräse S. J. Organomet. Chem. 691 (2006) 2171
5. Pye P.J., Rossen K., Reamer R.A., Volante R.P., and Reider P.J. Tetrahedron Lett. 39 (1998) 4441
6. Hou X.-L., Wu X.-W., Dai L.-X., Cao B.-X., and Sun J. Chem. Commun. (2000) 1195
7. Verdal N., Godbout J.T., Perkins T.L., Bartholomew G.P., Bazan G.C., and Kelly A.M. Chem. Phys. Lett. 320 (2000) 95
8. Bartholomew G.P., and Bazan G.C. J. Am. Chem. Soc. 124 (2002) 5183
9. Bartholomew G.P., and Bazan G.C. Acc. Chem. Res. 34 (2001) 30
10. Popova E.L., Rozenberg V.I., Starikova A., Keuker-Baumann S., Kitzerow H.S., and Hopf H. Angew. Chem., Ind. Ed. 41 (2002) 3411
11. Morisaki Y., and Chujo Y. Tetrahedron Lett. 46 (2005) 2533
12. Zyss J., Ledoux I., Volkov S., Chernyak V., Mukamel S., Bartholomew G.P., and Bazan G.C. J. Am. Chem. Soc. 122 (2000) 1195
13. Amthor S., Lambert C., Dümmler S., Fischer I., and Schelter J. J. Phys. Chem. A 110 (2006) 5204
14. Aly A.A., Ehrhardt S., Hopf H., Dix I., and Jones P.G. Eur. J. Org. Chem. (2006) 335
15. Hu W., Gompf B., Pflaum J., Schweitzer D., and Dressel M. Appl. Phys. Lett. 84 (2004) 4720
16. Ball P.J., Shtoyko T.R., Bauer J.A.K., Oldham W.J., and Connick W.B. Inorg. Chem. 43 (2004) 622
17. Hopf H., Sankararaman S., Dix I., Jones P.G., Alt H.G., and Licht A. Eur. J. Inorg. Chem. (2002) 123
18. Lahann J., Höcker H., and Langer R. Angew. Chem., Int. Ed. Engl. 40 (2001) 726
19. Hopf H., and Gleiter R. Modern Cyclophane Chemistry (2004), Wiley-VCH, Weinheim
20. de Meijere A., and König B. Synlett. 11 (1997) 1221
21. Sankararaman S., Hopf H., Dix I., and Jones P.G. Eur. J. Org. Chem. (2000) 2711
22. Bondarenko L., Dix I., Hinrichs H., and Hopf H. Synthesis (2004) 2751
23. Morisaki Y., and Chujo Y. Polymer Preprints 44 (2003) 980
24. Morisaki Y., and Chujo Y. Macromolecules 36 (2003) 9319
25. Bhalla R., Boxwell C., Duckett S.B., Dyson P.J., Humphrey D.G., Steed J.W., and Suman P. Organometallics 21 (2002) 924
26. Morisaki Y., and Chujo Y. Macromolecules 36 (2003) 9319
27. Gollas B., Speiser B., Zagos I., and Maichle-Mössmer C. J. Organomet. Chem. 602 (2000) 75
28. Elschenbroich C., Möckel R., and Zenneck U. Angew. Chem., Int. Ed. Engl. 17 (1978) 531
29. Bolm C., Wenz C., and Raabe G. J. Organomet. Chem. 662 (2002) 23
30. 2 see:. Maekawa M., Hashimoto N., Kuroda-Sowa T., Suenaga Y., and Munakata M. Inorg. Chim. Acta 328 (2002) 254
31. For metal complexes ligated with the PHANEPHOS ligand via a metal-phosphorus bond see:. Blazina D., Boxwell C., Duckett S.B., Dyson P.J., Scopelliti R., Steed J.W., and Suman P. Inorg. Chim. Acta 354 (2003) 4
32. Suman P., Dyer P.W., Dyson P.J., James S.L., and Steed J.W. New J. Chem. 22 (1998) 1311
33. Knorr M., Strohmann C., and Braunstein P. Organometallics 15 (1996) 5633
34. Knorr M., and Strohmann C. Eur. J. Inorg. Chem. (2000) 241
35. Knorr M., Jourdain I., Villafane F., and Strohmann C. J. Organomet. Chem. 690 (2005) 1456
36. Jourdain I., Vielle-Petit L., Clément S., Knorr M., Villafane F., and Strohmann C. Inorg. Chem. Commun. 9 (2006) 127
37. Morisaki Y., Fujimura F., and Chujo Y. Organometallics 22 (2003) 3553
38. Minuti L., Taticchi A., Marrocchi A., Landi S., and Gacs-Baitz E. G.-B. Tetrahedron Lett. 46 (2005) 5735
39. For the synthesis of a double layered 1,4-bis(phenyethynyl)-substituted PCP see:. König B., Knieriem B., and de Meijere A. Chem. Ber. 126 (1993) 1643
40. Corey E.J., and Fuchs P.L. Tetrahedron Lett. 36 (1972) 3769
41. Bland W.J., and Kemmit R.D.W. Eur. J. Chem. Soc. (A) (1968) 1278
42. Rajaram J., Person R.G., and Ibers J.A. J. Am. Chem. Soc. 96 (1974) 2103
43. Knorr M., Schmitt G., Kubiki M.M., and Vigier E. Eur. J. Inorg. Chem. (2003) 414
44. Gassman P.G., and Cesa I.G. Organometallics 3 (1984) 119
45. Davis J.A., and Dutremez S.G. Magnet. Res. Chem. 31 (1993) 439
46. Guyard L., and Audebert P. Electrochem. Commun. 3 (2001) 164
47. Salhi S., Lee B., Metz C., Bottomley L.A., and Collard D.M. Org. Lett. (2002) 3195
48. Guyard L., Dumas C., Miomandre F., Pansu R., Renault-Méallet R., and Audebert P. New. J. Chem. 6 (2003) 1000
49. Guyard L., An M.N.D., and Audebert P. Adv. Mat. 13 (2001) 133
50. Peindy H.N., Guyon F., Jourdain I., Knorr M., Schildbach D., and Strohmann C. Organometallics 25 (2006) 1472
51. Tsui J. Transition Metal Reagents and Catalysts, Innovations in Organic Synthesis (2000), Wiley, Chicester, New York
52. Chung Y.K. Coord. Chem. Rev. 188 (1999) 297
53. Buchholz H., Reiser O., and De Meijere A. Synlett 1 (1991) 20
54. Hübel W., and Hoogzand C. Chem. Ber. 93 (1960) 103
55. Krüerke U., and Hübel W. Chem. Ber. 94 (1961) 2829
56. Grotjahn D.B. In: Hegedus L.S. (Ed). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford 741-770
57. Tojo S., and Isobe M. Tetrahedron Lett. 46 (2005) 381
58. Akita M., Terada M., and Moro-Oka Y. Organometallics 11 (1992) 1825
59. Duffy N.W., Robinson B.H., and Simpson J. J. Organomet. Chem. 573 (1999) 36
60. Zhang Y.-H., Chen Z., Zhang W.-Q., Yin Y.-Q., Zhou Z.-Y., and Chan A.S.C. Synth. React Inorg. Metal-Org. Chem. 32 (2002) 1013
61. Champeil E., and Draper S.M. J. Chem. Soc., Dalton Trans. (2001) 1440
62. Hong F.-E., Tsai Y.-T., Chang Y.-C., and Tsao Ko B. Inorg. Chem. 40 (2001) 5487
63. Koentjoro O.F., Zuber P., Puschmann H., Goetta A.E., Howard J.A.K., and Low P.J. J. Organomet. Chem. 670 (2003) 178
64. Harris R.K. Nuclear Magnetic Resonance Spectroscopy: A Physiochemical view (1983), Pitman, London
65. Furlani A., Carusi P., and Russo M.V. J. Organomet. Chem. 67 (1974) 315
66. Koie Y., Shinoda S., and Saito Y. J. Chem. Soc., Dalton Trans. (1981) 1082
67. 2 fragment see:. Albrecht K., Hockless D.C.R., König B., Neumann H., Bennett M.A., and de Meijere A. Chem. Commun. (1996) 543
68. Fontaine X.L.R., Jacobsen G.B., Shaw B.L., and Thornton-Pett M. J. Chem. Soc., Dalton Trans. (1988) 741
69. Jacobsen G.B., Shaw B.L., and Thornton-Pett M. J. Chem. Soc., Dalton Trans. (1987) 3079
70. Pringle P.G., Shaw B.L., and Thornton-Pett M. J. Chem. Soc., Dalton Trans. (1983) 889
71. Ugi I., Werner B., and Dömling A. Molecules 8 (2003) 53
72. Ugi I. Isonitrile Chemistry (1971), Academic Press, New York
73. Zhou J. Eur. J. Org. Chem. (2003) 1133
74. Lee Y., Morales G.M., and Yu L. Angew. Chem., Int. Ed. Engl. 44 (2005) 4228
75. Henderson J.I., Feng S., Ferrence G.M., Bein T., and Kubiak C.P. Inorg. Chim. Acta 242 (1996) 115
76. Singleton E., and Oosthuisen H.E. Adv. Organomet. Chem. 22 (1983) 209
77. Lentz D. Angew. Chem., Int. Ed. Engl. 33 (1994) 1315
78. Hahn F.E. Angew. Chem., Int. Ed. Engl. 32 (1993) 650
79. Pombeiro A.J.L., Fatima M., Silva C.G.d., and Michelin R.A. Coord. Chem. Rev. 218 (2001) 43
80. Knorr M., and Strohmann C. Eur. J. Inorg. Chem. (1998) 495
81. Knorr M., and Strohmann C. Organometallics 18 (1999) 248
82. Braunstein P., Durand J., Knorr M., and Strohmann C. Chem. Commun. (2001) 211
83. Knorr M., Jourdain I., Crini G., Frank K., Sachdev H., and Strohmann C. Eur. J. Inorg. Chem. (2002) 2419
84. Knorr M., Jourdain I., Lentz P., Willemsen S., and Strohmann C. J. Organomet. Chem. 684 (2003) 216
85. Knorr M., Jourdain I., Braunstein P., Strohmann C., Tiripicchio A., and Ugozzoli F. J. Chem. Soc., Dalton Trans. (2006) 5248
86. Evrard D., Clément S., Lucas D., Hanquet B., Knorr M., Strohmann C., Decken A., Mugnier Y., and Harvey P.D. Inorg. Chem. 45 (2006) 1305
87. S. Clément, M. Knorr, C. Strohmann, J.-F. Bérubé, D. Fortin, F. Brisach, P.D. Harvey, The Photophysic of Dinuclear Isocyanide Complexes (in preparation).
88. Cipiciani A., Frinuelli F., Mancini V., Piermatti O., Pizzo F., and Ruzziconi R. J. Org. Chem. 62 (1997) 3744
89. Benner L.S., and Balch A.L. J. Am. Chem. Soc. 100 (1978) 6099
90. Grundy K.R., and Robertson K.N. Organometallics 2 (1993) 1736
91. 2+ [32a].
92. Howell J.A.S., Saillard J.-Y., Le Beuze A., and Jaouen G. J. Chem. Soc., Dalton Trans. (1982) 2533
93. Substituent effects on the frontier molecular orbitals of aryl isocyanides have been studied:. Johnston R.F., and Cooper J.C. J. Mol. Struct. (Theochem) 236 (1991) 297
94. Yam V.W.-W., Lau V.C.-Y., and Cheung K.-K. Organometallics 14 (1978) 2753
95. Long N.J., and Williams C.K. Angew. Chem., Int. Ed. Engl. 42 (2003) 2586
96. Hurst S.K., and Ren T. J. Organomet. Chem. 670 (2003) 188
97. Courmarcel J., Le Gland G., Toupet L., Paul F., and Lapinte C. J. Organomet. Chem. 670 (2003) 108
98. Paul F., Costuas K., Ledoux I., Deveau S., Zyss J., Halet J.-F., and Lapinte C. Organometallics 21 (2002) 5229
99. Ara I., Berenguer J.R., Eguizábal E., Forniés J., Gomez J., and Lalinde E. J. Organomet. Chem. 670 (2003) 221
100. Hurst S.K., Humphrey M.G., Morrall J.P., Cifuentes M.P., Samoc M., Luther-Davies B., Heath G.A., and Willis A.C. J. Organomet. Chem. 670 (2003) 56
101. Bruce M.I., de Montigny F., Jevric M., Lapinte C., Skelton B.W., Smith M.E., Heath G.A., and Whitec A.H. J. Organomet. Chem. 689 (2004) 2860
102. Ziessel R., and Diring S. Tetrahedron Lett 47 (2006) 4687
103. Olah G.A., and Arvanaghi M. Angew. Chem. 93 (1981) 925
104. Angew. Chem., Int. Ed. Engl. 22 (1981) 878
105. Blake D.M., and Roundhill D.M. Inorg. Synth. 18 (1978) 120
106. Sheldrick G.M. shelxl-97, Program for Crystal Structure Refinement (1997), University of Göttingen, Germany
107. Sheldrick G.M. shelxs-90, Program for Crystal Structure Solution (1990), University of Göttingen, Germany