Synthesis and reactivity of tungsten (II) methylene complexes

Organometallics

Volumn 16, Issue 22, 1997, Pages 4865-4874

  Gunnoe, T Brent ^a   Surgan, Matthew ^a   White, P S ^a   Templeton, J L ^a   Casarrubios, Luis ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001245544     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970470a     Document Type: Article

References (84)

1. Fischer, E. O.; Maasböl, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 580.
2. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
3. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
4. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
5. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
6. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
7. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
8. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
9. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
10. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
11. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
12. For metallocarbene reviews, see: (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 151. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (c) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121. (d) Doyle, M. P. Chem. Rev. 1986, 86, 919. (e) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (f) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield, FL, 1983. (g) Schrock, R. R. Science 1983, 219, 13. (h) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733. (i) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (j) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545. (k) Cotton, F. A.; Lukehart, C. M. Prog. Inorg. Chem. 1972, 16, 487.
13. For reviews of ROMP, see: refs 3-5 in Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
14. For reviews of olefin metathesis, see: (a) Ivin, J. J. Olefin Metathesis; Academic Press: New York, 1983. (b) Calderon, N.; Lawrence, J. P.; Ofstead, E. A. Adv. Organomet. Chem. 1979, 17, 449. (c) Grubbs, R. H. Comprehensive Organometallic Chemistry; Wilkinson, G. W., Stone, A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 499. (d) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100 and references therein.
15. For reviews of olefin metathesis, see: (a) Ivin, J. J. Olefin Metathesis; Academic Press: New York, 1983. (b) Calderon, N.; Lawrence, J. P.; Ofstead, E. A. Adv. Organomet. Chem. 1979, 17, 449. (c) Grubbs, R. H. Comprehensive Organometallic Chemistry; Wilkinson, G. W., Stone, A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 499. (d) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100 and references therein.
16. For reviews of olefin metathesis, see: (a) Ivin, J. J. Olefin Metathesis; Academic Press: New York, 1983. (b) Calderon, N.; Lawrence, J. P.; Ofstead, E. A. Adv. Organomet. Chem. 1979, 17, 449. (c) Grubbs, R. H. Comprehensive Organometallic Chemistry; Wilkinson, G. W., Stone, A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 499. (d) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100 and references therein.
17. For reviews of olefin metathesis, see: (a) Ivin, J. J. Olefin Metathesis; Academic Press: New York, 1983. (b) Calderon, N.; Lawrence, J. P.; Ofstead, E. A. Adv. Organomet. Chem. 1979, 17, 449. (c) Grubbs, R. H. Comprehensive Organometallic Chemistry; Wilkinson, G. W., Stone, A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 499. (d) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100 and references therein.
18. See, for example: (a) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1973, 95, 5833. (b) Casey, C. P.; Tuinstra, H. E.; Saeman, M. C. J. Am. Chem. Soc. 1976, 98, 608. (c) Casey, C. P.; Polichnowski, S. W. J. Am. Chem. Soc. 1977, 99, 6097.
19. See, for example: (a) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1973, 95, 5833. (b) Casey, C. P.; Tuinstra, H. E.; Saeman, M. C. J. Am. Chem. Soc. 1976, 98, 608. (c) Casey, C. P.; Polichnowski, S. W. J. Am. Chem. Soc. 1977, 99, 6097.
20. See, for example: (a) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1973, 95, 5833. (b) Casey, C. P.; Tuinstra, H. E.; Saeman, M. C. J. Am. Chem. Soc. 1976, 98, 608. (c) Casey, C. P.; Polichnowski, S. W. J. Am. Chem. Soc. 1977, 99, 6097.
21. Jolly, P. W.; Pettit, R. J. Am. Chem. Soc. 1966, 88, 5044.
22. See, for example: (a) Mango, F. D.; Dvoretzky, I. J. Am. Chem. Soc. 1966, 88, 1654. (b) Green, M. L. H.; Ishaq, M.; Whiteley, R. N. J. Chem. Soc. A 1967, 1508. (c) Collier, M. R.; Kingston, B. M.; Lappert, M. F. J. Chem. Soc. D (Chem. Commun.) 1970, 1498.
23. See, for example: (a) Mango, F. D.; Dvoretzky, I. J. Am. Chem. Soc. 1966, 88, 1654. (b) Green, M. L. H.; Ishaq, M.; Whiteley, R. N. J. Chem. Soc. A 1967, 1508. (c) Collier, M. R.; Kingston, B. M.; Lappert, M. F. J. Chem. Soc. D (Chem. Commun.) 1970, 1498.
24. See, for example: (a) Mango, F. D.; Dvoretzky, I. J. Am. Chem. Soc. 1966, 88, 1654. (b) Green, M. L. H.; Ishaq, M.; Whiteley, R. N. J. Chem. Soc. A 1967, 1508. (c) Collier, M. R.; Kingston, B. M.; Lappert, M. F. J. Chem. Soc. D (Chem. Commun.) 1970, 1498.
25. (a) Schrock, R. R. J. Am. Chem. Soc. 1975, 97, 6577.
26. (b) Guggenberger, L. J.; Schrock, R. R. J. Am. Chem. Soc. 1975, 97, 6578.
27. (c) Schrock, R. R.; Sharp, P. R. J. Am. Chem. Soc. 1978, 100, 2389.
28. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
29. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
30. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
31. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
32. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
33. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
34. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
35. For representative examples of other nucleophilic methylene carbenes, see: (a) Tour, J. M.; Bedworth, P. V.; Wu, R. Tetrahedron Lett. 1989, 30, 3927. (b) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (c) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. (d) Schwartz, J.; Gell, K. I. J. Organomet. Chem. 1980, 184, C1. (e) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. (f) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 700, 3611. (g) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. (h) Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640.
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49. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
50. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
51. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
52. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
53. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
54. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
55. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
56. For some representative examples of electrophilic methylene carbenes, see: (a) Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835. (b) Barefield, E. K.; McCarten, P.; Hillhouse, M. C. Organometallics 1985, 4, 1682. (c) Davison, A.; Krusell, W. C.; Michaelson, R. C. J. Organomet. Chem. 1974, 72, C7. (d) Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473. (e) O'Connor, E. J.; Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1987, 109, 3739. (f) Mattson, M. N.; Bays, J. P.; Zakutansky, J.; Stolarski, V.; Helquist, P. J. Org. Chem. 1989, 54, 2467. (g) Riley, P. E.; Capshew, C. E.; Pettit, R.; Davies, R. E. Inorg. Chem. 1978, 17, 408. (h) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
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