메뉴 건너뛰기




Volumn 102, Issue 15, 1980, Pages 5016-5025

Bond Fixation in Annulenes. 8. Assessment of the Ring Inversion and Bond Shifting Barriers in 1,2,3-TrimethyIcyclooctatetraene. Resolution, Absolute Configuration, and Circular Dichroic Behavior of an [8]Annulene Hydrocarbon1

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0004772610     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00535a032     Document Type: Article
Times cited : (24)

References (65)
  • 3
    • 85021535545 scopus 로고
    • 1952, 20, 65. Bastiansen, O.; Hedberg, L.; Hedberg, K. The Ohio State University Dissertatioin Fellow. 1957, 27, 1311. Traetteberg, M. Acta Chem. Scand.
    • Karle, I. L. J. Chem. Phys. 1952, 20, 65. Bastiansen, O.; Hedberg, L.; Hedberg, K. The Ohio State University Dissertatioin Fellow. 1957, 27, 1311. Traetteberg, M. Acta Chem. Scand. 1966, 20, 1724.
    • (1966) J. Chem. Phys. , vol.20 , pp. 1724
    • Karle, I.L.1
  • 5
    • 33947487883 scopus 로고
    • 1962, 84, 671. Anet, F. A. L.; Brown, A. J. R.; Lin, Y. S. Acta Crystallogr., Sect B.
    • Anet, F. A. L. J. Am. Chem. Soc. 1962, 84, 671. Anet, F. A. L.; Brown, A. J. R.; Lin, Y. S. Acta Crystallogr., Sect B. 1964, 86, 3576.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3576
    • Anet, F.A.L.1
  • 7
    • 0039971887 scopus 로고
    • 1965, 87, 2862. Buchanan, G. W. Tetrahedron Lett. 1972, 665. Luz, Z.; Meiboom, S. J. Chem. Phys.
    • Gwynn, D. E.; Whitesides, G. M.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 2862. Buchanan, G. W. Tetrahedron Lett. 1972, 665. Luz, Z.; Meiboom, S. J. Chem. Phys. 1973, 59, 1077.
    • (1973) J. Am. Chem. Soc. , vol.59 , pp. 1077
    • Gwynn, D.E.1    Whitesides, G.M.2    Roberts, J.D.3
  • 8
    • 0001743395 scopus 로고
    • Of course, if the side chain possesses a chiral center, ring inversion produces a diastereoisomer.
    • Of course, if the side chain possesses a chiral center, ring inversion produces a diastereoisomer. See: Anet, F. A. L.; Bock, L. A. J. Am. Chem. Soc. 1968, 90, 7130.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 7130
    • Anet, F.A.L.1    Bock, L.A.2
  • 9
    • 85021571130 scopus 로고
    • 1971, 25, 573(10) Allinger, N. L. J. Org. Chem.
    • Oth, J. F. M. Pure Appl. Chem. 1971, 25, 573(10) Allinger, N. L. J. Org. Chem. 1962, 27, 443.
    • (1962) Pure Appl. Chem. , vol.27 , pp. 443
    • Oth, J.F.M.1
  • 13
    • 85021552791 scopus 로고
    • 1973, 29 2519 15) Dewar, M. J. S.; Harget, A.; Haselbach, E. J. Am. Chem. Soc. 1969, 91, 7521. Internally conflicting results appear to exist relative to an earlier report: Dewar, M. J. S.; Gleicher, G. J. Chem. Phys. Lett.
    • Allinger, N. L.; Sprague, J. T.; Finder, C. J. Tetrahedron 1973, 29 2519 15) Dewar, M. J. S.; Harget, A.; Haselbach, E. J. Am. Chem. Soc. 1969, 91, 7521. Internally conflicting results appear to exist relative to an earlier report: Dewar, M. J. S.; Gleicher, G. J. Chem. Phys. Lett. 1965, 87, 685.
    • (1965) Tetrahedron , vol.87 , pp. 685
    • Allinger, N.L.1    Sprague, J.T.2    Finder, C.J.3
  • 20
    • 0004278143 scopus 로고
    • Verlag Chemie: Weinheim/Bergstr., West Germany
    • Reviews: (a) Schröder, G. “Cyclooctatetraen”; Verlag Chemie: Weinheim/Bergstr., West Germany, 1965.
    • (1965) Cyclooctatetraen
    • Schröder, G.1
  • 30
    • 85021570239 scopus 로고
    • 1972, 39, 330. Scholes, G.; Graham, C. R.; Brookhart, M. J. Am. Chem. Soc.
    • Howell, J. A. S.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Organomet. Chem. 1972, 39, 330. Scholes, G.; Graham, C. R.; Brookhart, M. J. Am. Chem. Soc. 1974, 96, 5665.
    • (1974) J. Organomet. Chem. , vol.96 , pp. 5665
    • Howell, J.A.S.1    Johnson, B.F.G.2    Josty, P.L.3    Lewis, J.4
  • 35
    • 85021587461 scopus 로고
    • Ph.D. Thesis, The Ohio State University
    • Taggart, D. L. Ph.D. Thesis, The Ohio State University, 1976.
    • (1976)
    • Taggart, D.L.1
  • 48
    • 33748888324 scopus 로고
    • Goering, H. L.; Eikenberry, J. N.; Koermer, G. S. J. Am. Chem. Soc. 1971, 93, 5913. 35) For examples of asymmetric induction of the Diels-Alder reaction, see: (a)
    • Goering, H. L.; Eikenberry, J. N.; Koermer, G. S. J. Am. Chem. Soc. 1971, 93, 5913. 35) For examples of asymmetric induction of the Diels-Alder reaction, see: (a) Walborsky, M. M.; Borash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333.
    • (1963) Tetrahedron , vol.19 , pp. 2333
    • Walborsky, M.M.1    Borash, L.2    Davis, T.C.3
  • 63
    • 85021590274 scopus 로고
    • 1961, 83, 4661. Jacobs, H. J. C.; Havinga, E. Reel. Trav. Chim. Pays-Bas 1965, 84, 932. Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105. Charney, E. “Introduction to Stereochemistry”. 1965, 21, 3126. Maestro, M.; Moccia, R.; Taddei, G. Theor. Chim. Acta 1967, 8, 80. Gould, R. R.; Hoffmann, R. J. Am. Chem. Soc. 1970, 92, 1813. Hug, W.; Wagniére, G. Helv. Chim. Acta 1971, 54, 633. Caldwell, D. J.; Eyring, H. “The Theory of Optical Activity”; Wiley-Interscience: New York, 1971;. Charney, E.; Edwards, J. M.; Weiss, U.; Ziffer, H. Tetrahedron 1972, 28, 973. Hug, W.; Wagniere, H. “Introduction to Stereochemistry”. 1972, 28, 1241. Nolle, H. J.; Buss, V. “Introduction to Stereochemistry”. 1975, 31, 719. Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc.
    • Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. J. Am. Chem. Soc. 1961, 83, 4661. Jacobs, H. J. C.; Havinga, E. Reel. Trav. Chim. Pays-Bas 1965, 84, 932. Weiss, U.; Ziffer, H.; Charney, E. Tetrahedron 1965, 21, 3105. Charney, E. “Introduction to Stereochemistry”. 1965, 21, 3126. Maestro, M.; Moccia, R.; Taddei, G. Theor. Chim. Acta 1967, 8, 80. Gould, R. R.; Hoffmann, R. J. Am. Chem. Soc. 1970, 92, 1813. Hug, W.; Wagniére, G. Helv. Chim. Acta 1971, 54, 633. Caldwell, D. J.; Eyring, H. “The Theory of Optical Activity”; Wiley-Interscience: New York, 1971; pp 223-232. Charney, E.; Edwards, J. M.; Weiss, U.; Ziffer, H. Tetrahedron 1972, 28, 973. Hug, W.; Wagniere, H. “Introduction to Stereochemistry”. 1972, 28, 1241. Nolle, H. J.; Buss, V. “Introduction to Stereochemistry”. 1975, 31, 719. Rosenfield, J. S.; Charney, E. J. Am. Chem. Soc. 1977, 99, 3209.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 223-232
    • Moscowitz, A.1    Charney, E.2    Weiss, U.3    Ziffer, H.4
  • 64
    • 85021592856 scopus 로고
    • 1970, 92, 7601. Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A.; Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3725. Beecham, A. F. J. Am. Chem. Soc. 1971, 27, 5207. Gawronski, J. K.; Kielczewski, H. A. Tetrahedron Lett. 1971, 2493. Scott, A. I.; Wrixon, A. D.; Tetrahedron 1971, 27, 4787. Andersen, N. H.; Costin, C. R.; Syrdal, D. D.; Svedberg, D. P. J. Am. Chem. Soc. 1973, 95, 2049. Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. J. Am. Chem. Soc. 1976, 98, 3015. Burgstahler, A. W.; Boger, D. L.; Naik, R. C. Tetrahedron
    • Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601. Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A.; Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3725. Beecham, A. F. J. Am. Chem. Soc. 1971, 27, 5207. Gawronski, J. K.; Kielczewski, H. A. Tetrahedron Lett. 1971, 2493. Scott, A. I.; Wrixon, A. D.; Tetrahedron 1971, 27, 4787. Andersen, N. H.; Costin, C. R.; Syrdal, D. D.; Svedberg, D. P. J. Am. Chem. Soc. 1973, 95, 2049. Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. J. Am. Chem. Soc. 1976, 98, 3015. Burgstahler, A. W.; Boger, D. L.; Naik, R. C. Tetrahedron 1976, 32, 309.
    • (1976) J. Am. Chem. Soc. , vol.32 , pp. 309
    • Burgstahler, A.W.1    Barkhurst, R.C.2
  • 65
    • 85021586870 scopus 로고
    • 1968, 48, 5037. Yaris, M.; Moscowitz, A.; Berry, R. S. J. Am. Chem. Soc. 1968, 49, 3150. Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695, 3706. Levin, C. C.; Hoffmann, R. J. Am. Chem. Soc. 1972, 94, 3446. Andersen, N. H.; Costin, C. R.; Shaw, J. R. J. Am. Chem. Soc.
    • Robin, M. R.; Basch, H.; Kuebler, N. A.; Kaplan, B. E.; Meinwald, J. J. Chem. Phys. 1968, 48, 5037. Yaris, M.; Moscowitz, A.; Berry, R. S. J. Am. Chem. Soc. 1968, 49, 3150. Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695, 3706. Levin, C. C.; Hoffmann, R. J. Am. Chem. Soc. 1972, 94, 3446. Andersen, N. H.; Costin, C. R.; Shaw, J. R. J. Am. Chem. Soc. 1974, 96, 3692.
    • (1974) J. Chem. Phys. , vol.96 , pp. 3692
    • Robin, M.R.1    Basch, H.2    Kuebler, N.A.3    Kaplan, B.E.4    Meinwald, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.