메뉴 건너뛰기




Volumn , Issue 11, 1999, Pages 2757-2762

The effect of pressure on retro Diels-Alder reactions

Author keywords

Activation volumes; High pressure chemistry; Packing coefficients; Reaction volumes; Retro Diels Alder reactions

Indexed keywords

ACID ANHYDRIDE; ANILINE DERIVATIVE; NITRILE;

EID: 0040164411     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2757::aid-ejoc2757>3.0.co;2-j     Document Type: Article
Times cited : (35)

References (54)
  • 5
    • 0001371814 scopus 로고    scopus 로고
    • The effect of pressure on organic reactions
    • R. van Eldik, C. D. Hubbard (Eds.), Wiley, New York, Spektrum, Heidelberg, chapter 3
    • [1e] M.K. Diedrich, A.E. Wigger, F.-G. Klärner, "The effect of pressure on organic reactions", in R. van Eldik, C. D. Hubbard (Eds.), Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997, chapter 3, p. 103-161.
    • (1997) Chemistry under Extreme or Non-Classical Conditions , pp. 103-161
    • Diedrich, M.K.1    Wigger, A.E.2    Klärner, F.-G.3
  • 6
    • 4244121462 scopus 로고    scopus 로고
    • The effect of pressure on reactions of dienes and polyenes
    • S. Patai, Z. Rappoport (Eds.), Wiley, New York, chapter 12
    • [1f] F.-G. Klärner, M.K. Diedrich, "The effect of pressure on reactions of dienes and polyenes" in S. Patai, Z. Rappoport (Eds.), The chemistry of functional groups, the chemistry of dienes and polyenes, Wiley, New York, 1997, vol. 1, chapter 12, p. 547-617.
    • (1997) The Chemistry of Functional Groups, the Chemistry of Dienes and Polyenes , vol.1 , pp. 547-617
    • Klärner, F.-G.1    Diedrich, M.K.2
  • 13
    • 0010485518 scopus 로고
    • [3d] W. J. le Noble, H. Kelm, Angew. Chem. 1980, 92, 887-904; Angew. Chem. Int. Ed. Engl. 1980, 19, 841.
    • (1980) Angew. Chem. , vol.92 , pp. 887-904
    • Le Noble, W.J.1    Kelm, H.2
  • 14
    • 2642611440 scopus 로고
    • [3d] W. J. le Noble, H. Kelm, Angew. Chem. 1980, 92, 887-904; Angew. Chem. Int. Ed. Engl. 1980, 19, 841.
    • (1980) Angew. Chem. Int. Ed. Engl. , vol.19 , pp. 841
  • 23
    • 0000631352 scopus 로고
    • Y. Li, K. N. Houk, J. Am. Chem. Soc. 1993, 115, 7478-7485; Review: K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711-739; Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7478-7485
    • Li, Y.1    Houk, K.N.2
  • 24
    • 0000631352 scopus 로고
    • Y. Li, K. N. Houk, J. Am. Chem. Soc. 1993, 115, 7478-7485; Review: K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711-739; Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
    • (1992) Angew. Chem. , vol.104 , pp. 711-739
    • Houk, K.N.1    Li, Y.2    Evanseck, J.D.3
  • 25
    • 33748960439 scopus 로고
    • Y. Li, K. N. Houk, J. Am. Chem. Soc. 1993, 115, 7478-7485; Review: K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711-739; Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 682
  • 30
    • 0003512063 scopus 로고
    • Ph. D. Dissertation, Ruhr-Universität Bochum, (F.-G. Klärner, Research Director)
    • w of ground states can also be calculated from tables of group contributions to the van der Waals volumes published by A. Bondi, J. Chem. Phys. 1964, 68, 441-451.
    • (1989) Cycloadditionen Unter Hohem Druck
    • Artschwager-Perl, U.1
  • 31
    • 20544433165 scopus 로고
    • w of ground states can also be calculated from tables of group contributions to the van der Waals volumes published by A. Bondi, J. Chem. Phys. 1964, 68, 441-451.
    • (1964) J. Chem. Phys. , vol.68 , pp. 441-451
    • Bondi, A.1
  • 32
    • 0012612517 scopus 로고
    • R. A. Grieger, C. A. Eckert, J. Am. Chem. Soc. 1970, 92, 2918-2919; R. A. Grieger, C. A. Eckert, J. Chem. Soc., Faraday Trans. 1970, 66, 2579-2584.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 2918-2919
    • Grieger, R.A.1    Eckert, C.A.2
  • 34
    • 0027104822 scopus 로고
    • According to recent quantum-mechanical calculations, the importance of secondary orbital interactions, which have also been frequently used to explain the endo diastereoselectivity of Diels-Alder reactions, seems to be questionable and to be reserved for special cases like the addition of cyclopropene to various dienes. T. Karcher, W. Sicking, J. Sauer, R. Sustmann, Tetrahedron Lett. 1992, 33, 8027-8030; R. Sustmann, W. Sicking, Tetrahedron 1992, 48, 10293-10300; Y. Apeloig, E. Matzner, J. Am. Chem. Soc. 1995, 117, 5375-5376.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8027-8030
    • Karcher, T.1    Sicking, W.2    Sauer, J.3    Sustmann, R.4
  • 35
    • 0026498168 scopus 로고
    • According to recent quantum-mechanical calculations, the importance of secondary orbital interactions, which have also been frequently used to explain the endo diastereoselectivity of Diels-Alder reactions, seems to be questionable and to be reserved for special cases like the addition of cyclopropene to various dienes. T. Karcher, W. Sicking, J. Sauer, R. Sustmann, Tetrahedron Lett. 1992, 33, 8027-8030; R. Sustmann, W. Sicking, Tetrahedron 1992, 48, 10293-10300; Y. Apeloig, E. Matzner, J. Am. Chem. Soc. 1995, 117, 5375-5376.
    • (1992) Tetrahedron , vol.48 , pp. 10293-10300
    • Sustmann, R.1    Sicking, W.2
  • 36
    • 0347196776 scopus 로고
    • According to recent quantum-mechanical calculations, the importance of secondary orbital interactions, which have also been frequently used to explain the endo diastereoselectivity of Diels-Alder reactions, seems to be questionable and to be reserved for special cases like the addition of cyclopropene to various dienes. T. Karcher, W. Sicking, J. Sauer, R. Sustmann, Tetrahedron Lett. 1992, 33, 8027-8030; R. Sustmann, W. Sicking, Tetrahedron 1992, 48, 10293-10300; Y. Apeloig, E. Matzner, J. Am. Chem. Soc. 1995, 117, 5375-5376.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5375-5376
    • Apeloig, Y.1    Matzner, E.2
  • 37
    • 0342876746 scopus 로고
    • Empirical calculations of molar volumes
    • W. J. le Noble (Ed.), Elsevier, Amsterdam, chapter 2
    • O. Exner, "Empirical Calculations of Molar Volumes", in W. J. le Noble (Ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988, chapter 2.
    • (1988) Organic High Pressure Chemistry
    • Exner, O.1
  • 41
    • 84963156495 scopus 로고
    • K. Cosstick, T. Asano, N. Ohno, High Pressure Res. 1992, 11, 37-54; T. Asano, H. Furuta, H. Sumi, J. Am. Chem. Soc. 1994, 116, 5545-5550; T. Asano, K. Matsuo, H. Sumi, Bull. Chem. Soc. Jpn. 1997, 70, 239-244.
    • (1992) High Pressure Res. , vol.11 , pp. 37-54
    • Cosstick, K.1    Asano, T.2    Ohno, N.3
  • 42
    • 0001295813 scopus 로고
    • K. Cosstick, T. Asano, N. Ohno, High Pressure Res. 1992, 11, 37-54; T. Asano, H. Furuta, H. Sumi, J. Am. Chem. Soc. 1994, 116, 5545-5550; T. Asano, K. Matsuo, H. Sumi, Bull. Chem. Soc. Jpn. 1997, 70, 239-244.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5545-5550
    • Asano, T.1    Furuta, H.2    Sumi, H.3
  • 43
    • 0000772178 scopus 로고    scopus 로고
    • K. Cosstick, T. Asano, N. Ohno, High Pressure Res. 1992, 11, 37-54; T. Asano, H. Furuta, H. Sumi, J. Am. Chem. Soc. 1994, 116, 5545-5550; T. Asano, K. Matsuo, H. Sumi, Bull. Chem. Soc. Jpn. 1997, 70, 239-244.
    • (1997) Bull. Chem. Soc. Jpn. , vol.70 , pp. 239-244
    • Asano, T.1    Matsuo, K.2    Sumi, H.3
  • 47
    • 84981838663 scopus 로고
    • O. De Lucchi, V. Lucchini, L. Pasquato, G. Modena, J. Org. Chem. 1984, 49, 596-604; C.A. Grob, H. Kny, A. Gagneux, Helv. Chim. Acta 1957, 40, 130-140.
    • (1957) Helv. Chim. Acta , vol.40 , pp. 130-140
    • Grob, C.A.1    Kny, H.2    Gagneux, A.3
  • 49
    • 84945922443 scopus 로고
    • K. Alder, R. Ruehmann, Justus Liebigs Ann. Chem. 1950, 566, 1; 15; D. Craig, J. J. Shipman, J. Kiehl, F. Widmer, R. Fowler, A. Hawthorne, J. Am. Chem. Soc. 1954, 76, 4573-4575.
    • (1950) Justus Liebigs Ann. Chem. , vol.566 , pp. 1
    • Alder, K.1    Ruehmann, R.2
  • 52
    • 25744452915 scopus 로고
    • [19a] M. Furdik, V. Sutoris, Chem. Zvesti. 1960, 14, 564-580; Chem. Abstr. 1961, 55, 16444c.
    • (1961) Chem. Abstr. , vol.55
  • 54
    • 25744455250 scopus 로고
    • [19b] M. Furdik, V. Sutoris, J. Suchey, Chem. Zvesti. 1961, 15, 490-495; Chem. Abstr. 1961, 55, 27137d.
    • (1961) Chem. Abstr. , vol.55


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.