Acylamino chromium carbene complexes: Direct carbonyl insertion, formation of munchnones, and trapping with dipolarophiles [7]

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7398-7399

  Merlic, Craig A ^a   Baur, Andreas ^a   Aldrich, Courtney C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CHROMIUM DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0034596317     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9934753     Document Type: Letter

References (48)

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4. For general reviews, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, Germany, 1983. (b) Wulff, W. D. In Comprehensive Organnmetallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds; Pergamon Press: New York, 1995; Vol. 12, pp 470-547. (c) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: Oxford, England, 1991; Vol. 5, pp 1065-1113.
5. For general reviews, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, Germany, 1983. (b) Wulff, W. D. In Comprehensive Organnmetallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds; Pergamon Press: New York, 1995; Vol. 12, pp 470-547. (c) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: Oxford, England, 1991; Vol. 5, pp 1065-1113.
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11. For reviews, see: (a) de Meijere, A. Pure Appl. Chem. 1996, 68, 61- 72. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381-390. (c) Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143- 153. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503-531.
12. For reviews, see: (a) de Meijere, A. Pure Appl. Chem. 1996, 68, 61- 72. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381-390. (c) Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143-153. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503-531.
13. For reviews, see: (a) de Meijere, A. Pure Appl. Chem. 1996, 68, 61- 72. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381-390. (c) Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143- 153. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503-531.
14. For general reviews, see: (a) Stefaniak, L.; Jazwinski, J. Khim. Geterotsikl. Soedin 1995, 1180-1199. (b) Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141. (c) Kobayashi, Y.; Kumadaki, I. Adv. Heterocycl. Chem. 1982, 31, 169-206. (d) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-122.
15. For general reviews, see: (a) Stefaniak, L.; Jazwinski, J. Khim. Geterotsikl. Soedin 1995, 1180-1199. (b) Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141. (c) Kobayashi, Y.; Kumadaki, I. Adv. Heterocycl. Chem. 1982, 31, 169-206. (d) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-122.
16. For general reviews, see: (a) Stefaniak, L.; Jazwinski, J. Khim. Geterotsikl. Soedin 1995, 1180-1199. (b) Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141. (c) Kobayashi, Y.; Kumadaki, I. Adv. Heterocycl. Chem. 1982, 31, 169-206. (d) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-122.
17. For general reviews, see: (a) Stefaniak, L.; Jazwinski, J. Khim. Geterotsikl. Soedin 1995, 1180-1199. (b) Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141. (c) Kobayashi, Y.; Kumadaki, I. Adv. Heterocycl. Chem. 1982, 31, 169-206. (d) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-122.
18. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
19. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1-C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
20. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
21. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
22. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
23. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
24. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
25. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
26. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
27. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
28. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
29. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
30. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
31. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
32. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
33. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
34. Pyrroles have been formed from reactions of group six Fischer carbene complexes, but by entirely different mechanisms: (a) Aumann, R.; Kuckert, E.; Krüger, C.; Angermund, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 6, 563-564. (b) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 389, C1- C6. (c) Aumann, R.; Heinen, H. J. Organomet. Chem. 1990, 391, C7-C11. (d) Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 2867-2870. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1990, 1238-1240. (g) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593. (h) Grotjahn, D. B.; Kroll, F. E. K.; Schäfer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (i) Aumann, R. Chem. Ber. 1993, 126, 2325-2330. (j) Aumann, R.; Jasper, B.; Goddard, R.; Krüger, C. Chem. Ber. 1994, 127, 717-724. (k) Funke, K.; Duetsch, M.; Stein, F.; Noltemeyer, M.; de Meijere, A. Chem. Ber. 1994, 127, 911-920. (l) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443-9444. (m) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J.-C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (n) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5027. (o) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580. (p) Aumann, R.; Yu, Z.; Fröhlich, R. Organometallics 1998, 17, 2897-2905. (q) Iwasawa, N.; Ochiai, T.; Maeyama, K. J. Org. Chem. 1998, 63, 3164-3165.
35. Hegedus, L. S.; Schultze, L. M.; Montgomery, J. Organometallics 1989, 8, 2189-2195.
36. A Pyrex pressure tube containing a solution of carbene complex and 2 equiv of alkyne in THF solvent was pressurized to 40 psi with CO. Photolysis was performed using a 450 W Hanovia medium-pressure mercury lamp and water cooling until the deep orange color of the carbene complex disappeared (2.5 h).
37. Complex 1a is an unstable red oil, but complex I1b forms stable olive-green needles. See Supporting Information.
38. For a recent review, see: Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288.
39. See Supporting Information.
40. Hexacarbonylchromium was isolated in 49% yield. Carbon dioxide was trapped with an aqueous barium hydroxide solution as barium carbonate in 88% yield.
41. (a) Bayer, H. O.; Huisgen, R.; Knorr, R.; Schaefer, F. C. Chem. Ber. 1970, 103, 2581-2597.
42. (b) Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Chem. Ber. 1970, 103, 2611-2624.
43. (c) Gotthardt, H.; Huisgen, R. Chem. Ber. 1970, 103, 2625-2638.
44. Powers, T. S.; Jiang, W.; Su, J.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 6438-6439 and references therein.
45. For a review, see: Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A. Curr. Org. Chem. 1998, 2, 551-574.
46. Alkynyl carbene complexes have been reacted with preformed mesoionic compounds: Choi, Y. H.; Kang, B. S.; Yoon, Y.-J.; Kim, J.; Shin, S. C. Synth. Commun. 1995, 25, 2043-2050.
47. (a) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 7418-7420.
48. (b) Merlic, C. A.; Roberts, W. M. Tetrahedron Lett. 1993, 34, 7379-7382.