Iridapyrrole complexes via formal 3 + 2 cycloaddition of iridium alkenyls to acetonitrile

Organometallics

Volumn 15, Issue 9, 1996, Pages 2192-2194

  Alvarado, Ysaias ^a   Daff, P James ^b   Pérez, Pedro J ^c   Poveda, Manuel L ^b   Sánchez Delgado, Roberto ^a   Carmona, Ernesto ^b  

^a INSTITUTO VENEZOLANO DE INVESTIGACIONES CIENTÍFICAS   (Venezuela)

^b CSIC   (Spain)

^c UNIVERSITY OF HUELVA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001077375     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950957o     Document Type: Article

References (56)

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16. See for example: (a) Feng, S. G.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 8613. (b) Feng, S. G.; White, P. S.; Templeton, J. L. Organometallics 1994, 13, 1214. (c) Endres, H. In Comprehensive Coordination Chemistry; Wilkinson, G., Guillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. II, Chapter 13.7.
17. See for example: (a) Feng, S. G.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1994, 116, 8613. (b) Feng, S. G.; White, P. S.; Templeton, J. L. Organometallics 1994, 13, 1214. (c) Endres, H. In Comprehensive Coordination Chemistry; Wilkinson, G., Guillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. II, Chapter 13.7.
18. 7: C, 43.00; H, 5.67; H, 16.72. Found: C, 43.58; H, 5.65; N, 15.02.
19. 7: C, 43.00; H, 5.67; H, 16.72. Found: C, 43.03; H, 5.65; N, 16.74.
20. 7: C, 48.64; H, 6.20; H, 14.71. Found: C, 49.04; H, 6.69; N, 14.23.
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26. This compound was obtained by following a procedure similar to that described above for 1.
27. See for example: (a) Bercaw, J. E.; Davies, D. L.; Wolczanski, P. T. Organometallics 1986, 5, 443. (b) Bochmann, M.; Wilson, L. M.; Hursthouse, M. B.; Motevalli, M. Organometallics 1988, 7, 1148. (c) Doxsee, K. M.; Mouser, J. K. M. Organometallics. 1990, 9, 3012. (d) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
28. See for example: (a) Bercaw, J. E.; Davies, D. L.; Wolczanski, P. T. Organometallics 1986, 5, 443. (b) Bochmann, M.; Wilson, L. M.; Hursthouse, M. B.; Motevalli, M. Organometallics 1988, 7, 1148. (c) Doxsee, K. M.; Mouser, J. K. M. Organometallics. 1990, 9, 3012. (d) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
29. See for example: (a) Bercaw, J. E.; Davies, D. L.; Wolczanski, P. T. Organometallics 1986, 5, 443. (b) Bochmann, M.; Wilson, L. M.; Hursthouse, M. B.; Motevalli, M. Organometallics 1988, 7, 1148. (c) Doxsee, K. M.; Mouser, J. K. M. Organometallics. 1990, 9, 3012. (d) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
30. See for example: (a) Bercaw, J. E.; Davies, D. L.; Wolczanski, P. T. Organometallics 1986, 5, 443. (b) Bochmann, M.; Wilson, L. M.; Hursthouse, M. B.; Motevalli, M. Organometallics 1988, 7, 1148. (c) Doxsee, K. M.; Mouser, J. K. M. Organometallics. 1990, 9, 3012. (d) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
31. The mechanism of this isomerization has not been investigated.
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38. The participation of the nitrite C-N multiple bond in organometallic reactions is relatively uncommon, although there are precedents in the literature. See for example: (a) Beckhaus, R.; Strauss, I.; Wagner, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 688. (b) Cohen, S. A.; Bercaw, J. E. Organometallics. 1985, 4, 1006. (c) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889. See also ref 10a,c. For pyridine synthesis involving formal coupling of two alkynes and nitriles: (d) Bonnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248. (e) Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 2211.
39. The participation of the nitrite C-N multiple bond in organometallic reactions is relatively uncommon, although there are precedents in the literature. See for example: (a) Beckhaus, R.; Strauss, I.; Wagner, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 688. (b) Cohen, S. A.; Bercaw, J. E. Organometallics. 1985, 4, 1006. (c) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889. See also ref 10a,c. For pyridine synthesis involving formal coupling of two alkynes and nitriles: (d) Bonnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248. (e) Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 2211.
40. The participation of the nitrite C-N multiple bond in organometallic reactions is relatively uncommon, although there are precedents in the literature. See for example: (a) Beckhaus, R.; Strauss, I.; Wagner, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 688. (b) Cohen, S. A.; Bercaw, J. E. Organometallics. 1985, 4, 1006. (c) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889. See also ref 10a,c. For pyridine synthesis involving formal coupling of two alkynes and nitriles: (d) Bonnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248. (e) Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 2211.
41. The participation of the nitrite C-N multiple bond in organometallic reactions is relatively uncommon, although there are precedents in the literature. See for example: (a) Beckhaus, R.; Strauss, I.; Wagner, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 688. (b) Cohen, S. A.; Bercaw, J. E. Organometallics. 1985, 4, 1006. (c) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889. See also ref 10a,c. For pyridine synthesis involving formal coupling of two alkynes and nitriles: (d) Bonnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248. (e) Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 2211.
42. The participation of the nitrite C-N multiple bond in organometallic reactions is relatively uncommon, although there are precedents in the literature. See for example: (a) Beckhaus, R.; Strauss, I.; Wagner, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 688. (b) Cohen, S. A.; Bercaw, J. E. Organometallics. 1985, 4, 1006. (c) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889. See also ref 10a,c. For pyridine synthesis involving formal coupling of two alkynes and nitriles: (d) Bonnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248. (e) Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 2211.
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45. 14 using a procedure similar to that already described for the Tp* analog 1.
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56. 17b). Although nitrile precoordination was suggested in some of these reactions, in no case was the simple adduct detected.