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Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2269-2273

The chemistry of 2-carbenabicyclo[3.2.1]octadiene: An ab-initio molecular orbital study

(2) Freeman, Peter K a Pugh, James K a

a OREGON STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CARBENABICYCLO[3.2.1]OCTA 3,6 DIENE; 3 CARBENATETRACYCLO[3.3.0.0. 2,8 0 4,6]OCTANE; AROMATIC HYDROCARBON; BICYCLO[3.2.1]OCTA 2,3,6 TRIENE; ENDO 6 (2 CARBENAVINYL)BICYCLO[3.1.0]HEX 2 ENE; ENDO 6 ETHYNYLBICYCLO[3.1.0]HEX 2 ENE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; ISOMERISM; REACTION ANALYSIS;

EID: 0033577358 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja9834428 Document Type: Article

Times cited : (14)

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- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1994) Advances in Carbene Chemistry , vol.1
- Brinker, U.¹

36
- 0004070677
- Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1978) Reactive Intermediates , vol.1
- Moss, R.A.¹ Jones Jr., M.²

37
- 0004070677
- Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1981) Reactive Intermediates , vol.2
- Moss, R.A.¹ Jones Jr., M.²

38
- 0002843719
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1994) Acc. Chem. Res. , vol.27 , pp. 287
- Liu, M.T.H.¹

39
- 0002216732
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1993) Acc. Chem. Res. , vol.26 , pp. 84
- Nickon, A.¹

40
- 0001136058
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1995) Acc. Chem. Res. , vol.28 , pp. 487
- Platz, M.S.¹

41
- 0001190191
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1985) Tetrahedron , vol.41 , pp. 1479
- Gaspar, P.P.¹ Hsu, P.² Chari, S.³ Jones, M.⁴

42
- 33847088460
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1977) Acc. Chem. Res. , vol.10 , pp. 353-359
- Jones, W.M.¹

43
- 0041054515
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1974) Acc. Chem. Res. , vol.7 , pp. 415-421
- Jones, W.M.¹

44
- 0016906449
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1976) Top. Curr. Chem. , vol.62 , pp. 173
- Wentrup, C.¹

45
- 0029987178
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2023
- Heinemann, C.¹ Müller, T.² Apeloig, Y.³ Schwarz, H.⁴

46
- 0029989970
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 1535
- Matzinger, S.¹ Bally, T.² Patterson, E.V.³ McMahon, R.J.⁴

47
- 0029868337
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3527
- Toscano, J.P.¹ Platz, M.S.²

48
- 0029992211
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3829
- Bonneau, R.¹ Liu, M.T.H.² Kim, K.C.³ Goodman, J.L.⁴

49
- 0029937183
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 5408
- Gonzalez, C.¹ Restrepo-Cossio, A.² Marquez, M.³ Wiberg, K.B.⁴

50
- 0011006404
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1996) J. Org. Chem. , vol.61 , pp. 1322
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- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1995) Liebigs Ann. , vol.10 , pp. 1721
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52
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- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1021
- Enders, D.¹ Breuer, K.² Raaabe, G.³ Runsink, J.⁴ Teles, J.H.⁵ Melder, J.P.⁶ Ebel, K.⁷ Brode, S.⁸

53
- 0000871511
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3685
- Armstrong, B.M.¹ Mckee, M.L.² Shevlin, P.B.³

54
- 0001324728
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 6376
- Tomioka, H.¹ Watanabe, T.² Hirai, K.³ Furukawa, K.⁴ Takui, I.⁵ Itoh, K.⁶

55
- 0030818024
- For reviews and leading references, see: (a) Mine, J. In Divalent Carbon; Ronald Press: 1964. (b) Kirmse, W. In Carbene Chemistry; Academic Press: New York, 1971. (c) Jones, M.; Moss, R. A. In Carbenes; Wiley: New York, 1973 and 1975; Vols. 1 and 2. (d) Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990. (e) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI: Greenwich, CT, 1994; Vol. 1. (f) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978; Vol. 1. Moss, R. A.; Jones, M., Jr. In Reactive Intermediates, Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1981; Vol. 2. (g) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287. (h) Nickon, A. Acc. Chem. Res. 1993, 26, 84. (i) Platz, M. S. Acc. Chem. Res. 1995, 28, 487. (j) Gaspar, P. P.; Hsu, P.; Chari, S.; Jones, M. Tetrahedron 1985, 41, 1479. (k) Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. (l) Jones, W. M. Acc. Chem. Res. 1974, 7, 415-421. (m) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (n) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023. (o) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1996, 118, 3527. (p) Bonneau, R., Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829. (q) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408. (r) Ashby, E. C.; Mehdizadeh, A.; Deshpande, A. K. J. Org. Chem. 1996, 61, 1322. (s) Kupfer, R. Brinker, U. H. Liebigs Ann. 1995, 10, 1721. (t) Enders, D.; Breuer, K.; Raaabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. (u) Armstrong, B. M.; Mckee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685. (v) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, I.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376. (w) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M., 1997, 119, 5682-5689. (x) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809. (y) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233-234. (z) Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088-1089.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 5682-5689
- Sulzbach, H.M.¹ Platz, M.S.² Schaefer III, H.F.³ Hadad, C.M.⁴

56
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