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Volumn , Issue 6, 1996, Pages 669-686

S(N)2' and 'S(N)2' like' ring openings of oxa-n-cyclo systems

Author keywords

allylic rearrangement; oxabicyclo; oxatricyclo; ring openening; S(N)2' reaction

Indexed keywords

CYCLOALKANE; NAPHTHALENE DERIVATIVE; ORGANIC COMPOUND; PHENOL DERIVATIVE;

EID: 0029793274     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4295     Document Type: Review
Times cited : (88)

References (84)
  • 1
    • 49149145492 scopus 로고
    • For recent reviews, see: Magid, R. M. Tetrahedron 1980, 36, 1901. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. Altenbach, H.-J. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 829. See also a small section within the following review on organocuprates: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
    • (1980) Tetrahedron , vol.36 , pp. 1901
    • Magid, R.M.1
  • 2
    • 0024302311 scopus 로고
    • For recent reviews, see: Magid, R. M. Tetrahedron 1980, 36, 1901. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. Altenbach, H.-J. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 829. See also a small section within the following review on organocuprates: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
    • (1989) Chem. Rev. , vol.89 , pp. 257
    • Consiglio, G.1    Waymouth, R.M.2
  • 3
    • 0001209842 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • For recent reviews, see: Magid, R. M. Tetrahedron 1980, 36, 1901. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. Altenbach, H.-J. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 829. See also a small section within the following review on organocuprates: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 829
    • Altenbach, H.-J.1
  • 4
    • 0000220284 scopus 로고
    • For recent reviews, see: Magid, R. M. Tetrahedron 1980, 36, 1901. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. Altenbach, H.-J. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 829. See also a small section within the following review on organocuprates: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
    • (1992) Org. React. , vol.41 , pp. 135
    • Lipshutz, B.H.1    Sengupta, S.2
  • 6
    • 9544255354 scopus 로고
    • Ph. D. Dissertation, California Institute of Technology
    • Winstein, S. Ph. D. Dissertation, California Institute of Technology, 1938.
    • (1938)
    • Winstein, S.1
  • 12
    • 0003536850 scopus 로고
    • Pergamon: Toronto, and references therein
    • Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: Toronto, 1983; pp 174-178 and references therein. Matassa, V. G.; Jenkins, P. R.; Kumin, A.; Damm, L.; Schreiber, J.; Felix, D.; Zass, E.; Eschenmoser, A. Isr. J. Chem. 1989, 29, 321.
    • (1983) Stereoelectronic Effects in Organic Chemistry , pp. 174-178
    • Deslongchamps, P.1
  • 15
  • 18
    • 0000260171 scopus 로고
    • and references therein
    • This argument has been used to explain 5-endo-trig reversals of 7-oxabicyclo[2.2.1] systems upon generation of an anion adjacent to an electron-withdrawing group, see: Keay, B. A.; Rajapaksa, D.; Rodrigo, R. Can. J. Chem. 1984, 62, 1093 and references therein.
    • (1984) Can. J. Chem. , vol.62 , pp. 1093
    • Keay, B.A.1    Rajapaksa, D.2    Rodrigo, R.3
  • 32
    • 33750863208 scopus 로고
    • Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem. 1993, 105, 267; Angew. Chem., Int. Ed. Engl. 1993, 32, 281.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 281
  • 33
    • 0002073767 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1968) J. Organomet. Chem. , vol.12
    • Eisch, J.J.1    Foxton, M.W.2
  • 34
    • 0000340776 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1973) Angew. Chem. , vol.85 , pp. 1002
    • Fischer, K.1    Jonas, K.2    Misbach, P.3    Stabba, R.4    Wilke, G.5
  • 35
    • 84981905416 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1973) Angew. Chem., Int. Ed. Engl. , vol.12 , pp. 943
  • 36
    • 9544248203 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7276
    • Eisch, J.J.1    Rhee, S.-G.2
  • 37
    • 0010743762 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1983) J. Organomet. Chem. , vol.250 , pp. 63
    • Eisch, J.J.1    Fichter, K.C.2
  • 38
    • 0001285755 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1988) Angew. Chem. , vol.100 , pp. 189
    • Wilke, G.1
  • 39
    • 84985614901 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 185
  • 40
    • 0001740306 scopus 로고
    • Eisch, J. J., Foxton, M. W. J. Organomet. Chem. 1968, 12, P33. Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem. 1973, 85, 1002; Angew. Chem., Int. Ed. Engl. 1973, 12, 943. Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Wilke, G. Angew. Chem. 1988, 100, 189; Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
    • (1990) J. Organomet. Chem. , vol.382 , pp. 273
    • Eisch, J.J.1    Sexsmith, S.R.2    Fichter, K.C.3
  • 42
    • 0029043023 scopus 로고
    • Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4185
    • Lautens, M.1    Ma, S.2    Yee, A.3
  • 53
    • 0024469904 scopus 로고
    • Arjona, O.; Fernández de la Pradilla, R.; Garcia, E.; Martin-Domenech, A.; Plumet, J. Tetrahedron Lett. 1989, 30, 6437. Arjona, O.; Fernández de la Pradilla, R.; Manzano, C.; Pérez, S.; Plumet, J. Tetrahedron Lett. 1987, 28, 5547. Arjona, O.; Fernández de la Pradilla, R.; Mallo, A.; Perez, S.: Plumet, J. J. Org. Chem. 1989, 54, 4158.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6437
    • Arjona, O.1    Fernández De La Pradilla, R.2    Garcia, E.3    Martin-Domenech, A.4    Plumet, J.5
  • 54
    • 1542608862 scopus 로고
    • Arjona, O.; Fernández de la Pradilla, R.; Garcia, E.; Martin-Domenech, A.; Plumet, J. Tetrahedron Lett. 1989, 30, 6437. Arjona, O.; Fernández de la Pradilla, R.; Manzano, C.; Pérez, S.; Plumet, J. Tetrahedron Lett. 1987, 28, 5547. Arjona, O.; Fernández de la Pradilla, R.; Mallo, A.; Perez, S.: Plumet, J. J. Org. Chem. 1989, 54, 4158.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5547
    • Arjona, O.1    Fernández De La Pradilla, R.2    Manzano, C.3    Pérez, S.4    Plumet, J.5
  • 55
    • 0000361392 scopus 로고
    • Arjona, O.; Fernández de la Pradilla, R.; Garcia, E.; Martin-Domenech, A.; Plumet, J. Tetrahedron Lett. 1989, 30, 6437. Arjona, O.; Fernández de la Pradilla, R.; Manzano, C.; Pérez, S.; Plumet, J. Tetrahedron Lett. 1987, 28, 5547. Arjona, O.; Fernández de la Pradilla, R.; Mallo, A.; Perez, S.: Plumet, J. J. Org. Chem. 1989, 54, 4158.
    • (1989) J. Org. Chem. , vol.54 , pp. 4158
    • Arjona, O.1    Fernández De La Pradilla, R.2    Mallo, A.3    Perez, S.4    Plumet, J.5
  • 71
    • 0000875294 scopus 로고
    • Hunt, I. R.; Rogers, C.; Woo, S.; Rauk, A.; Keay, B. A. J. Am. Chem. Soc. 1995, 117, 1049. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Synlett 1991, 353.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 1049
    • Hunt, I.R.1    Rogers, C.2    Woo, S.3    Rauk, A.4    Keay, B.A.5
  • 72
    • 0000875294 scopus 로고
    • Hunt, I. R.; Rogers, C.; Woo, S.; Rauk, A.; Keay, B. A. J. Am. Chem. Soc. 1995, 117, 1049. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Synlett 1991, 353.
    • (1992) Can. J. Chem. , vol.70 , pp. 2929
    • Rogers, C.1    Keay, B.A.2
  • 73
    • 0025995752 scopus 로고
    • Hunt, I. R.; Rogers, C.; Woo, S.; Rauk, A.; Keay, B. A. J. Am. Chem. Soc. 1995, 117, 1049. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Synlett 1991, 353.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6477
    • Rogers, C.1    Keay, B.A.2
  • 74
    • 0000875294 scopus 로고
    • Hunt, I. R.; Rogers, C.; Woo, S.; Rauk, A.; Keay, B. A. J. Am. Chem. Soc. 1995, 117, 1049. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Synlett 1991, 353.
    • (1991) , pp. 353
    • Rogers, C.1    Synlett, K.B.A.2
  • 75
    • 0003127879 scopus 로고    scopus 로고
    • Woo, S.; Keay, B. A. Synlett 1996, 135. Rhodes, A.; Frantes, K. H.; Boothroyd, B.; McGonagle, M. P.; Crosse, R. Nature (London) 1961, 192, 952.
    • (1996) Synlett , pp. 135
    • Woo, S.1    Keay, B.A.2


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