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Volumn 27, Issue 7, 2008, Pages 1534-1541

Fluoride-promoted aryl and allyl migration from boron to tin in 1-stannyl-2-borylferrocenes

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACIDS; ORGANOBORANES; ORGANOTIN REAGENTS; TRANSMETALATION REACTIONS;

EID: 42449154624     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700967a     Document Type: Article
Times cited : (21)

References (88)
  • 1
    • 26344460493 scopus 로고
    • Houben-Weyl, G. Thieme Verlag: Stuttgart, New York
    • (a) Köster, R. Methods of Organic Chemistry (Houben-Weyl); G. Thieme Verlag: Stuttgart, New York, 1982; Vol. 13/3a.
    • (1982) Methods of Organic Chemistry , vol.13 3a
    • Köster, R.1
  • 4
    • 42449159545 scopus 로고    scopus 로고
    • Kaufmann, D. E., Matteson, D. S., Eds. Organometallics: Boron Compounds; G. Thieme Verlag: Stuttgart, New York, 2004; Science of Synthesis 6.
    • (d) Kaufmann, D. E., Matteson, D. S., Eds. Organometallics: Boron Compounds; G. Thieme Verlag: Stuttgart, New York, 2004; Science of Synthesis Vol. 6.
  • 7
    • 2842517972 scopus 로고    scopus 로고
    • 4] for the qualitative and quantitative determination of organotin species in aqueous medium through conversion to the ethylated tetraorganotin derivatives has been described; see: Carlier-Pinasseau, C.; Lespes, G.; Astruc, M. Appl. Organomet. Chem. 1996, 10, 505-512.
    • 4] for the qualitative and quantitative determination of organotin species in aqueous medium through conversion to the ethylated tetraorganotin derivatives has been described; see: Carlier-Pinasseau, C.; Lespes, G.; Astruc, M. Appl. Organomet. Chem. 1996, 10, 505-512.
  • 15
    • 0004063249 scopus 로고    scopus 로고
    • 2nd ed, Wiley-VCH: Weinheim, Germany
    • Davies, A. G. Organotin Chemistry; 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Organotin Chemistry
    • Davies, A.G.1
  • 22
    • 84985738584 scopus 로고    scopus 로고
    • Heteronuclear bidentate Lewis acids with stannyl and boryl groups attached to vinylene, phenylene, and naphthalene scaffolds have been reported. See ref 14 and: (a) Köster, R, Seidel, G, Boese, R, Wrackmeyer, B. Chem. Ber. 1988, 121, 597-615
    • Heteronuclear bidentate Lewis acids with stannyl and boryl groups attached to vinylene, phenylene, and naphthalene scaffolds have been reported. See ref 14 and: (a) Köster, R.; Seidel, G.; Boese, R.; Wrackmeyer, B. Chem. Ber. 1988, 121, 597-615.
  • 27
    • 0000719399 scopus 로고    scopus 로고
    • For related studies with 1-stannyl-2-borylbenzene derivatives, see
    • For related studies with 1-stannyl-2-borylbenzene derivatives, see: Eisch, J. J.; Kotowicz, B. W. Eur. J. Inorg. Chem. 1998, 761-769.
    • (1998) Eur. J. Inorg. Chem , pp. 761-769
    • Eisch, J.J.1    Kotowicz, B.W.2
  • 31
    • 3042546217 scopus 로고    scopus 로고
    • For related work with Hg/B heteronuclear bidentate Lewis acids see: (a) Solé, S.; Gabbaï, F. P. Chem. Commun. 2004, 1284-1285.
    • For related work with Hg/B heteronuclear bidentate Lewis acids see: (a) Solé, S.; Gabbaï, F. P. Chem. Commun. 2004, 1284-1285.
  • 33
    • 27544481166 scopus 로고    scopus 로고
    • For examples of Sn-Cl for Sn-F exchange, see: (a) Krause, E. Ber. Dtsch. Chem. Ges. 1918, 51, 1447-1456
    • For examples of Sn-Cl for Sn-F exchange, see: (a) Krause, E. Ber. Dtsch. Chem. Ges. 1918, 51, 1447-1456.
  • 37
    • 42449092283 scopus 로고    scopus 로고
    • Treatment of 1-Cl with KF under similar conditions resulted in full recovery of the starting material, indicating that transfer of alkyl groups does not occur under these conditions.
    • Treatment of 1-Cl with KF under similar conditions resulted in full recovery of the starting material, indicating that transfer of alkyl groups does not occur under these conditions.
  • 40
    • 42449142804 scopus 로고    scopus 로고
    • - (3-Ph).
    • - (3-Ph).
  • 43
    • 13644270486 scopus 로고    scopus 로고
    • Related literature complexes: (a) Groux, L. F.; Weiss, T.; Reddy, D. N.; Chase, P. A.; Piers, W. E.; Ziegler, T.; Parvez, M.; Benet-Buchholz, J. J. Am. Chem. Soc. 2005, 127, 1854-1869.
    • Related literature complexes: (a) Groux, L. F.; Weiss, T.; Reddy, D. N.; Chase, P. A.; Piers, W. E.; Ziegler, T.; Parvez, M.; Benet-Buchholz, J. J. Am. Chem. Soc. 2005, 127, 1854-1869.
  • 45
    • 0036013182 scopus 로고    scopus 로고
    • Defluoridation of potassium fluoroborates can be accomplished by treatment with fluoride anion acceptors, a With BF3; Frohn, H.-J, Bailly, F, Bardin, V. V. Z. Anorg. Allg. Chem. 2002, 628, 723-724
    • 3; Frohn, H.-J.; Bailly, F.; Bardin, V. V. Z. Anorg. Allg. Chem. 2002, 628, 723-724.
  • 46
    • 0035583385 scopus 로고    scopus 로고
    • 5: Frohn, H.-J.; Bardin, V. V. Z. Anorg. Allg. Chem. 2001, 627, 15-16.
    • 5: Frohn, H.-J.; Bardin, V. V. Z. Anorg. Allg. Chem. 2001, 627, 15-16.
  • 47
    • 33751155775 scopus 로고    scopus 로고
    • 3SiCl: Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020-3027.
    • 3SiCl: Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020-3027.
  • 48
    • 20444399909 scopus 로고    scopus 로고
    • 3SiOTf: Burgos, C. H.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 8044-8049.
    • 3SiOTf: Burgos, C. H.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 8044-8049.
  • 59
    • 42449157851 scopus 로고    scopus 로고
    • Not surprisingly, these intermolecular reactions proceed considerably more slowly at the temperature of 45°C used for the synthesis of compounds 2-R.
    • Not surprisingly, these intermolecular reactions proceed considerably more slowly at the temperature of 45°C used for the synthesis of compounds 2-R.
  • 61
    • 42449094363 scopus 로고    scopus 로고
    • Indeed, the mixture with KF in the absence of 18-crown-6 remains turbid throughout the reaction, indicating the presence of insoluble potassium salts.
    • Indeed, the mixture with KF in the absence of 18-crown-6 remains turbid throughout the reaction, indicating the presence of insoluble potassium salts.
  • 62
    • 0035930009 scopus 로고    scopus 로고
    • For recent examples of anion binding to organoboranes see: a
    • For recent examples of anion binding to organoboranes see: (a) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2001, 123, 11372-11375.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 11372-11375
    • Yamaguchi, S.1    Akiyama, S.2    Tamao, K.3
  • 85
    • 42449090052 scopus 로고    scopus 로고
    • 119Sn NMR chemical shifts of 95.4 ppm for the former and 130.8 ppm for the latter.
    • 119Sn NMR chemical shifts of 95.4 ppm for the former and 130.8 ppm for the latter.
  • 88
    • 42449115088 scopus 로고    scopus 로고
    • Sheldrick, G. M. SHELXTL, Version 6.14; Bruker AXS, Inc, Madison, WI, 2004
    • Sheldrick, G. M. SHELXTL, Version 6.14; Bruker AXS, Inc., Madison, WI, 2004.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.