Abstract
During the past 12 years, we have been engaged in a comprehensive study (chiefly by infrared and nuclear magnetic resonance techniques) of rotational isomerism in carbonyl-containing derivatives of furan, thiophene, and pyrrole. In this review, we draw together the spectroscopic aspects of this work and discuss the conclusions by individual ring system and functional group type.
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Literature cited
K.-I. Dahlqvist and S. Forsen, J. Phys. Chem., 69, 4062 (1965).
B. P. Roques and S. Combrisson, Can. J. Chem., 51, 573 (1973).
M. L. Martin, J.-C. Roze, G. J. Martin, and P. Fournari, Tetrahedron Lett., 3407 (1970).
S. Nagata, T. Yamabe, K. Yoshikawa, and H. Kato, Tetrahedron, 219, 2545 (1973).
R. J. Abraham and T. M. Siverns, Tetrahedron, 28, 3015 (1972).
D. J. Chadwick, G. D. Meakins, and E. E. Richards, Tetrahedron Lett., 3183 (1974).
F. Monnig, H. Dreizler, and H. O. Rudolf, Z. Naturforsch., 21a, 1633 (1966).
D. J. Chadwick and G. D. Meakins, Chem. Commun., 637 (1970).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Chem. Commun., 742 (1972).
C. G. Andrieu, C. Chatain-Cathand, M.-C. Fournie-Zaluski, and B. Roques, C. R. Hebd. Seances Acad. Sci., Ser. C, 275, 559 (1972).
K. Kovalenko, V. I. Minkin, Z. N. Nazarova, and D. V. Kazachenko, Zh. Obshch. Khim., 32, 549 (1962).
H. Lumbroso, D.-M. Bertin, and P. Cagniat, Bull. Soc. Chim. Fr., 1720 (1970).
G. Allen and H. J. Bernstein, Can. J. Chem., 33, 1055 (1955).
R. J. Abraham and M. A. Cooper, Chem. Commun., 588 (1966).
D. J. Chadwick, J. Chambers, P. K. G. Hodgson, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans., 1, 1141 (1974).
F. J. Chadwick, J. Chambers, H. E. Hargraves, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans., 1, 2327 (1973).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans. 2, 13 (1975).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans., 1, 1766 (1973).
L. J. Bellamy, Advances in Infrared Group Frequencies, Methuen, London (1968).
S. Combrisson, B. Roques, P. Rigny, and J. J. Bassilier, Can. J. Chem., 49, 904 (1971).
L. Arlinger, K.-I. Dahlqvist, and S. Forsen, Acta Chem. Scand., 24, 662 (1970).
R. L. Snowden, Ph. D. Thesis, Oxford (1973).
B. P. Roques and M. C. Fournie-Zaluski, Org. Magn. Reson., 3, 305 (1971).
J. W. ApSimon, P. V. Demasco, D. W. Mathieson, W. G. Craig, A. Karim, L. Saunders, and W. B. Whalley, Tetrahedron, 26, 119 (1970).
D. J. Chadwick, J. Chem. Soc. Perkin Trans. 2, 451 (1976).
K.-I. Dahlqvist and S. Forsen, J. Phys. Chem., 69, 1760 (1965).
D. J. Chadwick, J. Chambers, R. Macrae, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 2, 597 (1976).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 1, 523 (1975).
M. Oki and H. Nakanishi, Bull. Chem. Soc. J., 43, 2558 (1970).
M. Oki and H. Nakanishi, Bull. Chem. Soc. J., 44, 3144 (1971).
M. Oki and H. Nakanishi, Bull. Chem. Soc. J., 44, 3197 (1971).
J. S. Byrne, P. F. Jackson, and K. J. Morgan, J. Chem. Soc. Perkin Trans 2, 845 (1973).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 2, 1959 (1972).
R. Mierzecki, Acta Physiol. Pol., 25, 797 (1964).
K. O. Hartman, G. L. Carlson, R. E. Witkowski, and W. G. Fately, Spectrochim Acta, 24A. 157 (1968).
D. J. Chadwick, J. Chambers, R. Macrae, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 2, 597: Supplementary Publication Number SUP 21625 (1976).
G. J. Karabatsos and D. J. Fenoglio, J. Am. Chem. Soc., 91, 1124, 3572, 3577 (1969).
K. Kalliorinne, Suom. Kemistil. B, 42B, 424 (1969).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 2, 1 (1976).
K. Schaumberg, J. Magn. Reson., 7, 177 (1972).
D. J. Chadwick, J. Chambers, and R. L. Snowden, J. Chem. Soc. Perkin Trans. 2, 1181 (1974).
D. J. Chadwick, Tetrahedron Lett., 679 (1975).
R. D. Schuetz and G. R. Nilles, J. Org. Chem., 36, 2188 (1971).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans. 2, 604 (1975).
P. Chiorboli and A. M. Drusiani, Atti. Accad. Naz. Lincei. Rend. Cl. Sci. Fis. Mat. Nat., 12, 309 (1952).
M. S. De Groot and J. Lamb, Proc. R. Soc. London, Ser. A, 242, 36 (1957).
H. Lumbroso and P. Pastour, C. R. Hebd. Seances Acad. Sci., 261, 1279 (1965).
H. Lumbroso, D-M. Bertin, M. Robba, and B. Roques, C. R. Hebd. Seances Acad. Sci., Ser. C, 262, 36 (1966).
F. Monnig, H. Dreizler, and H. D. Rudolf, Z. Naturforsch., 20a, 1323 (1965).
M. L. Martin, C. Andrieu, and G. J. Martin, Bull. Soc. Chim. Fr., 698 (1968).
L. Kaper and Th. J. De Boer, Recl. Trav. Chim., 89, 825 (1970).
C. Andrieu, R. Pinel, and Y. Mollier, Bull. Soc. Chim. Fr., 1314 (1971).
B. Antoine, J.-J. Peron, P. Saumagne, and R. Guilard, J. Chim. Phys., 68, 232 (1971).
J. Chambers, Ph. D. Thesis, Oxford (1973).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 1, 2079 (1972).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans 1, 201 (1973).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc. Perkin Trans, 1, 1141 (1974).
D. J. Chadwick, J. Chambers, G. D. Meakins, S. E. Musgrave, and R. L. Snowden, J. Chem. Res. (S), 26 (1977); J. Chem. Res. (M), 0385 (1977).
C. Goldenberg and F. Binon, Bull. Soc. Chim. Fr., 75, 129 (1966).
B. P. Roques, S. Combrisson, C. Riche, and C. Pascard-Billy, Tetrahedron, 26, 3555 (1970).
G. Marino, J. Heterocycl. Chem., 9, 817 (1972).
P. Mirone and V. Lorenzelli, Ann. Chim. (Italy), 48, 72 (1958).
P. Mirone and V. Lorenzelli, Ann. Chim. (Italy), 49, 59 (1959).
R. A. Jones and A. G. Moritz, Spectrochim. Acta, 21, 295 (1965).
D. J. Chadwick, G. D. Meakins, and C. A. Rhodes, J. Chem. Res. (S), 42 (1980); J. Chem. Res. (M), 0878–0886 (1980).
C. L. Chang, I. G. John, G. L. D. Ritchie, and P. Gore, J. Chem. Soc. Perkin Trans. 2, 1318 (1974).
B. P. Roques, S. Combrisson, and F. Wehrli, Tetrahedron Lett., 1047 (1975).
D. J. Chadwick and I. A. Cliffe, J. Chem. Soc. Perkin Trans 2, 737 (1980).
L. J. Bellamy, The Infrared Spectra of Complex Molecules, Chapman and Hall, London (1975).
C. Jaureguiberry, M. C. Fournie-Zaluski, and S. Combrisson, Org. Magn. Reson., 5, 165 (1973).
M. Farnier and T. Drakenberg, J. Chem. Soc. Perkin Trans. 2, 337 (1975).
D. J. Chadwick, J. Chambers, G. D. Meakins, R. L. Snowden, J. Chem. Soc., Perkin Trans. 2, 1959 (1972).
D. J. Chadwick, J. Chambers, G. D. Meakins, R. L. Snowden, J. Chem. Soc., Perkin Trans, 1, 523 (1975).
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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 579–612, May, 1984.
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Chadwick, D.J., Cliffe, I.A. Contributions to the study of rotational isomerism in derivatives of furan, thiophene, and pyrrole bearing carbonyl-containing substituents (review). Chem Heterocycl Compd 20, 461–488 (1984). https://doi.org/10.1007/BF00514296
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DOI: https://doi.org/10.1007/BF00514296