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Volumn 37, Issue 21, 1972, Pages 3248-3254

Grignard Reagents from Bromobenzo[h]quinolmes. 13-Substituted Derivatives of 20-Chloronaphtho[2′,1′ : 12,13](2,4)pyridinophane

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EID: 0007354173     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00986a013     Document Type: Article
Times cited : (9)

References (40)
  • 1
    • 0004223231 scopus 로고
    • The methylene-bridged aromatic compounds in this study are named using the rules described by Academic Press, New York, N. Y.
    • The methylene-bridged aromatic compounds in this study are named using the rules described by B. H. Smith in “Bridged Aromatic Compounds,” Academic Press, New York, N. Y., 1964.
    • (1964) Bridged Aromatic Compounds
    • Smith, B.H.1
  • 2
    • 85022284110 scopus 로고
    • There does not exist a universally aocepted method for the naming of such compounds; cf. Chemical Abstracts' name for 3b, for example, is 15-bromo-20-chloro-3,4,5,6,7,8,9,10,11,12-decahydro-2,13-metheno-13H-l-naphtho[1,2-b]azacyclopentadecene
    • There does not exist a universally aocepted method for the naming of such compounds; cf. F. Vogtle and P. Newmann, Tetrahedron, 26, S847 (1970). Chemical Abstracts' name for 3b, for example, is 15-bromo-20-chloro-3,4,5,6,7,8,9,10,11,12-decahydro-2,13-metheno-13H-l-naphtho[1,2-b]azacyclopentadecene.
    • (1970) Tetrahedron , vol.26 , pp. S847
    • Vogtle, F.1    Newmann, P.2
  • 3
    • 0007355679 scopus 로고
    • The pyridinophane ring is asymmetric since the methylene bridge cannot flip to the opposite face. Cf.
    • The pyridinophane ring is asymmetric since the methylene bridge cannot flip to the opposite face. Cf. W. E. Parham, R. W. Davenport, and J. B. Biasotti, Tetrahedron Lett., 557 (1969);
    • (1969) Tetrahedron Lett. , pp. 557
    • Parham, W.E.1    Davenport, R.W.2    Biasotti, J.B.3
  • 6
    • 0000513112 scopus 로고
    • For alternative schemes see (a)
    • For alternative schemes see (a) R. E. Lutz, et al., J. Amer. Chem. Soc., 68, 1813 (1946);
    • (1946) J. Amer. Chem. Soc. , vol.68 , pp. 1813
    • Lutz, R.E.1
  • 13
    • 0000141194 scopus 로고
    • obtained a low yield of diphenyl-(2-quinolyl)carbinol from 2-bromoquinoline but concluded that the use of Grignard reagents in the quinoline series was not of preparative value
    • J. P. Wibaut and L. G. Heeringa, Recl. Trav. Chim. Pays-Bas, 74, 1003 (1955), obtained a low yield of diphenyl-(2-quinolyl)carbinol from 2-bromoquinoline but concluded that the use of Grignard reagents in the quinoline series was not of preparative value;
    • (1955) Recl. Trav. Chim. Pays-Bas , vol.74 , pp. 1003
    • Wibaut, J.P.1    Heeringa, L.G.2
  • 15
    • 0014260316 scopus 로고
    • Quinoline lithium reagents have been successfully used for this purpose. Cf. (a)
    • Quinoline lithium reagents have been successfully used for this purpose. Cf. (a) A. Burger and R. N. Pinder, J. Med. Chem., 11, 267 (1968);
    • (1968) J. Med. Chem. , vol.11 , pp. 267
    • Burger, A.1    Pinder, R.N.2
  • 21
    • 0000513112 scopus 로고
    • reported that 2,8-disubstituted quinolines do not lead to stable hydrobromides, presumably for steric reasons
    • R. E. Lutz, et al., J. Amer. Chem. Soc., 68, 1813 (1946), reported that 2,8-disubstituted quinolines do not lead to stable hydrobromides, presumably for steric reasons.
    • (1946) J. Amer. Chem. Soc. , vol.68 , pp. 1813
    • Lutz, R.E.1
  • 24
    • 33947484148 scopus 로고
    • It has been shown (ref 3) that substituents on the α-methylene carbon atom in the pyridinophane structure are resistant to SN1 and SN2 reactions, and it has been suggested that steric factors do not favor stabilization of a developing carbonium ion (sp2 carbon) at this center. Similarly, one would not expect carbanions to be easily formed at this position have shown that, as the ring size in paracyclophanes is decreased, the acidity of benzylic methylene is decreased
    • It has been shown (ref 3) that substituents on the α-methylene carbon atom in the pyridinophane structure are resistant to SN1 and SN2 reactions, and it has been suggested that steric factors do not favor stabilization of a developing carbonium ion (sp2 carbon) at this center. Similarly, one would not expect carbanions to be easily formed at this position. D. J. Cram and L. A. Singer, J. Amer. Chem. Soc., 85, 1084 (1963), have shown that, as the ring size in paracyclophanes is decreased, the acidity of benzylic methylene is decreased.
    • (1963) J. Amer. Chem. Soc. , vol.85 , pp. 1084
    • Cram, D.J.1    Singer, L.A.2
  • 40
    • 85022275172 scopus 로고
    • Sadtler Research Laboratories, Philadelphia, Pa.
    • “Sadtler Index of Infrared Spectra,” Sadtler Research Laboratories, Philadelphia, Pa., 1967, No. S691K.
    • (1967) Sadtler Index of Infrared Spectra , Issue.S691K


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.