Free radical reactions for heterocycle synthesis. Part 6: 2-Bromobenzoic acids as building blocks in the construction of nitrogen heterocycles

Tetrahedron

Volumn 59, Issue 17, 2003, Pages 3009-3018

  Zhang, Wei ^a,b   Pugh, Georgia ^a  

^a DUPONT COMPANY   (United States)

^b Fluorous Technologies Inc   (United States)

Author keywords

Nitrogen heterocycles; Pharmacophores; Radical cyclization

Indexed keywords

2 BROMOBENZOIC ACID; ACID; AROMATIC COMPOUND; BENZOIC ACID DERIVATIVE; BICYCLO COMPOUND; BRIDGED COMPOUND; CHLORIDE; FREE RADICAL; HETEROCYCLIC COMPOUND; HYDROGEN; ISOCOUMARIN DERIVATIVE; ISOINDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; LACTAM DERIVATIVE; NITROGEN DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CONJUGATE; CYCLIZATION; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL;

EID: 0037459880     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00381-8     Document Type: Article

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53. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
54. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
55. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
56. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
57. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
58. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
59. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
60. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
61. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
62. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
63. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
64. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
65. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
66. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
67. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
68. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
69. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
70. Representative references on intramolecular homolytic ipso substitutions: (a) Zhang W., Pugh G. Synlett. 2002;778 (b) Ryokawa A., Togo H. Tetrahedron. 57:2001;5915 (c) Leardini R., McNab H., Minozzi M., Nanni D. J. Chem. Soc., Perkin Trans. 1. 2001;1072 (d) Amrein S., Bossart M., Vasella T., Studer A. J. Org. Chem. 65:2000;4281 (e) Bonfand E., Forslund L., Motherwell W.B., Vazquez S. Synlett. 2000;475 (f) Caddick S., Shering C.L., Wadman S.N. Tetrahedron. 56:2000;465 (g) Miranda L.D., Cruz-Almanza R., Alvarez-García A., Muchowski J.M. Tetrahedron Lett. 41:2000;3035 (h) Clive D.L., Kang S. Tetrahedron Lett. 41:2000;1315 (i) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Org. Lett. 2:2000;1899 (j) Clark A.J., De Campo F., Deeth R.J., Filik R.P., Gatard S., Hunt N.A., Lastecoueres D., Thomas G.H., Verlhac J.-B., Wongtap H. J. Chem. Soc., Perkin Trans. 1. 2000;671 (k) Senboku H., Hasegawa H., Orito K., Tokuda M. Tetrahedron Lett. 41:2000;5699 (l) Alcaide B., Rodriguez-Vicente A. Tetrahedron Lett. 39:1998;6589 (m) Amii H., Kondo S., Uneyama K. J. Chem. Soc., Chem. Commun. 1998;1845 (n) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S. Tetrahedron. 53:1997;285 (o) Giraud L., Lacote E., Renaud P. Helv. Chim. Acta. 80:1997;2148 (p) Mander L.N., Sherburn M.S. Tetrahedron Lett. 37:1996;4255 (q) Lee E., Whang H.S., Chung C.K. Tetrahedron Lett. 36:1995;913 (r) Black M., Cadogan J.I.G., McNab H. J. Chem. Soc., Chem. Commun. 1990;395 (s) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;631 (t) Kohler J.J., Speckamp W.N. Tetrahedron Lett. 1977;635.
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