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Volumn 36, Issue 11, 1997, Pages 1164-1170

Alkenylidenes in Organic Synthesis

Author keywords

Carbenes; Carbenoids; Cyclizations; Rearrangements; Synthetic methods

Indexed keywords


EID: 0030739039     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711641     Document Type: Review
Times cited : (132)

References (140)
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 321-322
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2587-2590
    • Taber, D.F.1    Song, Y.2
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
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    • Taber, D.F.1    You, K.K.2
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4745-4748
    • Doyle, M.P.1    Zhou, Q.-L.2    Raab, C.E.3    Roos, G.H.P.4
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7579-7582
    • Doyle, M.P.1    Zhou, Q.-L.2    Dyatkin, A.B.3    Ruppar, D.A.4
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1995) J. Org. Chem. , vol.60 , pp. 6654-6655
    • Doyle, M.P.1    Protopopova, M.N.2    Zhou, Q.-L.3    Bode, J.W.4    Simonsen, S.H.5    Lynch, V.6
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 547-556
    • Taber, D.F.1    You, K.K.2    Rheingold, A.L.3
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1371-1374
    • Doyle, M.P.1    Kalinin, A.V.2
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
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    • Recent papers: a) E. Lee, I. Choi, S. Y. Song, J. Chem. Soc. Chem. Commun. 1995, 321-322; b) D. F. Taber, Y. Song, Tetrahedron Lett. 1995, 36, 2587-2590; c) M. P. Doyle, A. B. Dyatkin, J. Org. Chem. 1995, 60, 3035-3038; d) D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762; e) M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, Tetrahedron Lett. 1995, 36, 4745-4748; f) M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin, D. A. Ruppar, ibid. 1995, 36, 7579-7582; g) M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. W. Bode, S. H. Simonsen, V. Lynch, J. Org. Chem. 1995, 60, 6654-6655; h) D. F. Taber, K. K. You, A. L. Rheingold, J. Am. Chem. Soc. 1996, 118, 547-556; i) M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374; k) C. F. Garcia, M. A. McKervey, T. Ye, Chem. Commun. 1996, 1465-1466; l) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706-6712; m) M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846; n) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, ibid. 1996, 61, 9146-9155.
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    • Doyle, M.P.1    Kalinin, A.V.2    Ene, D.G.3
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    • Alkenylidenes generated by α-elimination of HX or by dediazonization show similar reactivities toward π bonds: a) P. J. Stang, M. G. Mangum, J. Am. Chem. Soc. 1975, 97, 6478-6481; b) D. P. Fox, J. A. Bjork, P. J. Stang, J. Org. Chem. 1983, 48, 3994-4002; c) J. C. Gilbert, D. H. Giamalva, ibid. 1992, 57, 4185-4188; d) M. Ochiai, T. Sueda, K. Uemura, Y. Masaki, ibid. 1995, 60, 2624-2626.
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