메뉴 건너뛰기




Volumn , Issue 2, 2009, Pages 238-252

Paracyclophanes: Extending the bridges. Reactions

Author keywords

m.n Paracyclophanes; Acylation; Aromatic substitution; Cyclophanes; Elctrophilic substitution; Regioselectivity; Transannular reactions

Indexed keywords


EID: 58649116253     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800748     Document Type: Article
Times cited : (5)

References (31)
  • 1
    • 58649089195 scopus 로고    scopus 로고
    • Z. Pechlivanidis, H. Hopf, L. Ernst, Eur. J. Org. Chem. 2008, 000-000, preceding paper.
    • Z. Pechlivanidis, H. Hopf, L. Ernst, Eur. J. Org. Chem. 2008, 000-000, preceding paper.
  • 6
    • 0002605142 scopus 로고
    • Eds, P. M. Keehn, S. M. Rosenfeld, Academic Press, New York
    • D. J. Cram in Cyclophanes (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983, vol. 1, pp. 1-21.
    • (1983) Cyclophanes , vol.1 , pp. 1-21
    • Cram, D.J.1
  • 7
    • 58649094475 scopus 로고    scopus 로고
    • D. Stalke, private communication. H. Hope, J. Bernstein, K. N. Trueblood, Acta Crystallogr., Sect. B 1972, 28, 1733-1744.
    • D. Stalke, private communication. H. Hope, J. Bernstein, K. N. Trueblood, Acta Crystallogr., Sect. B 1972, 28, 1733-1744.
  • 11
    • 58649098003 scopus 로고    scopus 로고
    • The calculations were carried out by employing the M05-2X functional and the 6-311+G(d,p) basis set.
    • The calculations were carried out by employing the M05-2X functional and the 6-311+G(d,p) basis set.
  • 13
    • 58649122935 scopus 로고    scopus 로고
    • The acetylation of 10 was first studied by Cram and Sheehan who obtained 18 in a yield of 51% at room temperature: D. J. Cram, M. Sheehan, J. Am. Chem. Soc. 1969, 91, 3544-3552.
    • The acetylation of 10 was first studied by Cram and Sheehan who obtained 18 in a yield of 51% at room temperature: D. J. Cram, M. Sheehan, J. Am. Chem. Soc. 1969, 91, 3544-3552.
  • 14
    • 0007835426 scopus 로고    scopus 로고
    • The acetylation of 12 has also already been studied by Cram and Kierstead who reported a yield of 88% for 21 when the reaction was carried out at room temp. for 70 min: D. J. Cram, R. W. Kierstead, J. Am. Chem. Soc. 1955, 77, 1186-1190. Our results are given in the table in Scheme 2 to allow a better comparison of the acetylation experiments. In numerous studies we have noted that Friedel-Crafts acylation with acetyl chloride/aluminum trichloride strongly depends on the quality and amount of the catalyst as well as on the reaction conditions (solvent, reaction time, temperature). However, both the original results and our experiments clearly show decreasing reactivity on going from 7 to 12.
    • The acetylation of 12 has also already been studied by Cram and Kierstead who reported a yield of 88% for 21 when the reaction was carried out at room temp. for 70 min: D. J. Cram, R. W. Kierstead, J. Am. Chem. Soc. 1955, 77, 1186-1190. Our results are given in the table in Scheme 2 to allow a better comparison of the acetylation experiments. In numerous studies we have noted that Friedel-Crafts acylation with acetyl chloride/aluminum trichloride strongly depends on the quality and amount of the catalyst as well as on the reaction conditions (solvent, reaction time, temperature). However, both the original results and our experiments clearly show decreasing reactivity on going from 7 to 12.
  • 15
    • 58649086989 scopus 로고    scopus 로고
    • More examples of this deshielding effect of bridge protons by functional groups anchored in a neighboring aromatic position are reported in B. Kaiser, Ph. D. Thesis, Technische Universität Braunschweig, 1993
    • More examples of this deshielding effect of bridge protons by functional groups anchored in a neighboring aromatic position are reported in B. Kaiser, Ph. D. Thesis, Technische Universität Braunschweig, 1993.
  • 16
    • 58649099448 scopus 로고
    • Diploma Thesis, Technische Universität Braunschweig
    • Z. Pechlivanidis, Diploma Thesis, Technische Universität Braunschweig, 1989.
    • (1989)
    • Pechlivanidis, Z.1
  • 23
    • 33645677074 scopus 로고    scopus 로고
    • For a review of superphanes, see:, Eds, R. Gleiter, H. Hopf, Wiley-VCH, Weinheim, chapter 4, pp
    • For a review of superphanes, see: R. Gleiter, R. Roers in, Modern Cyclophane Chemistry (Eds.: R. Gleiter, H. Hopf), Wiley-VCH, Weinheim, 2004, chapter 4, pp. 105-129.
    • (2004) Modern Cyclophane Chemistry , pp. 105-129
    • Gleiter, R.1    Roers, R.2
  • 24
    • 0005571208 scopus 로고
    • For a review of multibridged cyclophanes, see:, Eds, P. M. Keehn, S. M. Rosenfeld, Academic Press, New York, chapter 9, pp
    • For a review of multibridged cyclophanes, see: H. Hopf in Cyclophanes (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983, chapter 9, pp. 521-572.
    • (1983) Cyclophanes , pp. 521-572
    • Hopf, H.1
  • 27
    • 58649106047 scopus 로고
    • unpublished results
    • L. Ernst, 1988, unpublished results.
    • (1988)
    • Ernst, L.1
  • 28
    • 58649084186 scopus 로고    scopus 로고
    • L. Ernst, Liebigs Ann. 1995, 13-16; Correction: Liebigs Ann. 1996, 153.
    • L. Ernst, Liebigs Ann. 1995, 13-16; Correction: Liebigs Ann. 1996, 153.
  • 29
    • 58649085734 scopus 로고    scopus 로고
    • MMX87, Serena Software, Box 3076, Bloomington, IN 47402, USA, 1987.
    • MMX87, Serena Software, Box 3076, Bloomington, IN 47402, USA, 1987.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.