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Volumn 64, Issue 19, 1999, Pages 6999-7008

Self-assembly of 3-[4'-(diethylboryl)phenyl]pyridine and 3-[3'- (diethylboryl)phenyl]pyridine: Synthesis, structural features, and stability in solution

Author keywords

[No Author keywords available]

Indexed keywords

3 [3' (DIETHYLBORYL)PHENYL]PYRIDINE; 3 [4' (DIETHYLBORYL)PHENYL]PYRIDINE; OLIGOMER; ORGANOBORON DERIVATIVE; PYRIDINE DERIVATIVE; SOLVENT; TOLUENE; UNCLASSIFIED DRUG;

EID: 0033578858     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981632v     Document Type: Article
Times cited : (18)

References (51)
  • 24
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    • The synthetic method described in this paper involves the stannylation of 3-bromopyridine by trimethylstannylsodium in 87% yield
    • (b) Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 1731. The synthetic method described in this paper involves the stannylation of 3-bromopyridine by trimethylstannylsodium in 87% yield.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 1731
    • Yamamoto, Y.1    Yanagi, A.2
  • 25
    • 37049114502 scopus 로고
    • Several methods for the synthesis of 6 have appeared in the literature, (a) p-Bromophenylation of pyridine by the Gomberg-Hey reaction: Abramovitch, R. A.; Saha, M. J. Chem. Soc. B 1966, 733.
    • (1966) J. Chem. Soc. B , pp. 733
    • Abramovitch, R.A.1    Saha, M.2
  • 26
    • 0344197820 scopus 로고
    • U.S. Patent 5,225,438, Jul 6
    • (b) Coupling reaction of 3-(diethylboryl)pyridine and 1,4-dibromobenzene in the presence of palladium catalyst: Dowell, R. I.; Edwards, P. N.; Oldham, K. U.S. Patent 5,225,438, Jul 6, 1993.
    • (1993)
    • Dowell, R.I.1    Edwards, P.N.2    Oldham, K.3
  • 27
    • 0345060124 scopus 로고    scopus 로고
    • U.S. Patent 5,554,613, Sep 10
    • Coupling reaction of p-bromoaniline and pyridine with added sodium nitrite and hydrochloric acid: Mallion, K. B. U.S. Patent 5,554,613, Sep 10, 1996.
    • (1996)
    • Mallion, K.B.1
  • 28
    • 0345491679 scopus 로고    scopus 로고
    • U.S. Patent 5,780,473, Jul 14
    • Coupling reaction of 3-bromopyridine and 4-bromophenylboronic acid in the presence of palladium catalyst: Murugesan, N.; Banish, J. C.; Stein, P. D. U.S. Patent 5,780,473, Jul 14, 1998. Our approach is different from the method described in the above literature.
    • (1998)
    • Murugesan, N.1    Banish, J.C.2    Stein, P.D.3
  • 29
    • 0344629506 scopus 로고
    • European Patent Application, No. 481,662 A1, Apr 22
    • The preparation of 7 has been already reported: Guthikonda, R. N.; Schmitt, S. M.; Dininno, F. P. European Patent Application, No. 481,662 A1, Apr 22, 1992. In this patent, 7 was prepared by the reaction of 3-bromopyridine with 3-bromophenylboronic acid in the presence of palladium catalyst in low yield (35%).
    • (1992)
    • Guthikonda, R.N.1    Schmitt, S.M.2    Dininno, F.P.3
  • 35
    • 0344197818 scopus 로고    scopus 로고
    • note
    • Measurements in the absence of salt did not give the peaks due to the oligomers comprised of 3. Moreover, in acetone either in the presence or absence of lithium chloride, or in toluene in the absence of lithium chloride, 3 also did not give the assignable peaks by means of either positive or negative polarity mode.
  • 36
    • 0344197819 scopus 로고    scopus 로고
    • note
    • A very small amount of proton signals also consists of one set of the signals as a monomer.
  • 37
    • 0344629501 scopus 로고    scopus 로고
    • note
    • 8, this signal would arise from a small amount of species such as a monomer or acyclic low molecular weight aggregates, which were free from the B-N coordination bond.
  • 38
    • 0344197817 scopus 로고    scopus 로고
    • note
    • As an alternative interpretation, a reviewer made a comment that more than one set of peaks may indicate a cyclic aggregate where the units are inequivalent. However, it appears that the concentration-and solvent-dependent NMR shifts as described in the section on NMR spectroscopy could not be explained by this interpretation.
  • 39
    • 0345491676 scopus 로고    scopus 로고
    • note
    • c, the interconversion should be fast enough to equilibrate them at room temperature.
  • 40
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    • note
    • 2 proton as being on the inside.
  • 46
    • 0344197813 scopus 로고    scopus 로고
    • note
    • In parentheses were shown the stabilization energy or THC value of another cyclic oligomer of two stable ones.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.