Stereocontrol in nickel mediated syntheses of cyclobutabenzenes. The selective preparation of cis and trans derivatives of 7,8-dibromocyclobutabenzene

Tetrahedron

Volumn 54, Issue 7, 1998, Pages 1207-1220

  Stanger, Amnon ^a   Shachter, Alona ^a   Boese, Roland ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; NICKEL;

ARTICLE; CIS ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; TRANS ISOMER;

EID: 0032510170     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10219-8     Document Type: Article

References (24)

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3. 1. Winters, M.P.; Stranberg, M.; Moore, H.W. J. Org. Chem., 1994, 59, 7572-7574; Kametani, T.; Suzuki, Y.; Honda, T. Heterocydes, 1985, 23(2), 305-308; Bush, E.J.; Jones, D.W.; Thornton-Pett, M. Tett. Lett. 1994, 35(52), 9755-9758; Wheeler, D.M.S.; Wheeler, M.M. Studies in Natural. Chem. 1994, 14, 3-46; Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600; Hahn, S.F.; Martin, S.J.; McKelvy, M.L.; Patrick, D.W. Macromolecules, 1993, 26, 3870-3877; Fishback, T.L.; Farona, M.F. J.Poly. Sci. 1993, 31A, 2747-2750; Kirchhoff, R.A.; Carriere, C.J.; Bruza, K.J.; Rondan, N.G.; Sammler, R.L. J. Macromol. Sci. Chem. 1991, A28(11&12), 1079-1113; Endo, T.; Koizumi, T.; Takata, T.; Chino, K. J.Poly. Sci. 1995, 33A, 707-715.
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5. 1. Winters, M.P.; Stranberg, M.; Moore, H.W. J. Org. Chem., 1994, 59, 7572-7574; Kametani, T.; Suzuki, Y.; Honda, T. Heterocydes, 1985, 23(2), 305-308; Bush, E.J.; Jones, D.W.; Thornton-Pett, M. Tett. Lett. 1994, 35(52), 9755-9758; Wheeler, D.M.S.; Wheeler, M.M. Studies in Natural. Chem. 1994, 14, 3-46; Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600; Hahn, S.F.; Martin, S.J.; McKelvy, M.L.; Patrick, D.W. Macromolecules, 1993, 26, 3870-3877; Fishback, T.L.; Farona, M.F. J.Poly. Sci. 1993, 31A, 2747-2750; Kirchhoff, R.A.; Carriere, C.J.; Bruza, K.J.; Rondan, N.G.; Sammler, R.L. J. Macromol. Sci. Chem. 1991, A28(11&12), 1079-1113; Endo, T.; Koizumi, T.; Takata, T.; Chino, K. J.Poly. Sci. 1995, 33A, 707-715.
6. 1. Winters, M.P.; Stranberg, M.; Moore, H.W. J. Org. Chem., 1994, 59, 7572-7574; Kametani, T.; Suzuki, Y.; Honda, T. Heterocydes, 1985, 23(2), 305-308; Bush, E.J.; Jones, D.W.; Thornton-Pett, M. Tett. Lett. 1994, 35(52), 9755-9758; Wheeler, D.M.S.; Wheeler, M.M. Studies in Natural. Chem. 1994, 14, 3-46; Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600; Hahn, S.F.; Martin, S.J.; McKelvy, M.L.; Patrick, D.W. Macromolecules, 1993, 26, 3870-3877; Fishback, T.L.; Farona, M.F. J.Poly. Sci. 1993, 31A, 2747-2750; Kirchhoff, R.A.; Carriere, C.J.; Bruza, K.J.; Rondan, N.G.; Sammler, R.L. J. Macromol. Sci. Chem. 1991, A28(11&12), 1079-1113; Endo, T.; Koizumi, T.; Takata, T.; Chino, K. J.Poly. Sci. 1995, 33A, 707-715.
7. 1. Winters, M.P.; Stranberg, M.; Moore, H.W. J. Org. Chem., 1994, 59, 7572-7574; Kametani, T.; Suzuki, Y.; Honda, T. Heterocydes, 1985, 23(2), 305-308; Bush, E.J.; Jones, D.W.; Thornton-Pett, M. Tett. Lett. 1994, 35(52), 9755-9758; Wheeler, D.M.S.; Wheeler, M.M. Studies in Natural. Chem. 1994, 14, 3-46; Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600; Hahn, S.F.; Martin, S.J.; McKelvy, M.L.; Patrick, D.W. Macromolecules, 1993, 26, 3870-3877; Fishback, T.L.; Farona, M.F. J.Poly. Sci. 1993, 31A, 2747-2750; Kirchhoff, R.A.; Carriere, C.J.; Bruza, K.J.; Rondan, N.G.; Sammler, R.L. J. Macromol. Sci. Chem. 1991, A28(11&12), 1079-1113; Endo, T.; Koizumi, T.; Takata, T.; Chino, K. J.Poly. Sci. 1995, 33A, 707-715.
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10. 2. Duval, D.; Hennig, P.; Bouchet, J.P.; Vian, J.; Peglion, J.L.; Volland, J.P.; Platzer, N.; Guilhem, J. Magn. Reson. Chem. 1997, 35, 175-183.
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20. 10. Stanger, A.; Schachter, A.; Boese, R. manuscript in preparation.
21. 11. Including 50 equivalents of DMF.
22. 12. The mechanism postulated for nickel mediated coupling reactions involves two species of the type C-Ni-Br that disproportionate to give the coupling product (C-C), Ni(II) and Ni(0). See Yamamoto, T.; Wakabayashi, S.; Osakada, K. J. J. Organomet. Chem. 1992, 428, 223-237.
23. 13. (a) As shown by the extensive studies of Mislow et. al. for isopropyl substituted benzene systems (see: Singh, M.D.; Siegel, J.; Biali, S.E.; Mislow, K. J. Am. Chem. Soc. 1987, 109, 3397-3402.).
24. 2 is partially positive and the bromine atoms are partially negative, the "gear effect" in 1,2-bis(dibromomethyl) should be stronger than in 1,2-bis(i-propyl)benzene. (b) See also Berg, U.; Liljefors, T.; Roussel, C.; Sandström, J. Acc. Chem. Res. 1985, 18, 80-86.