Conformational Analysis. XXIII. 1,3-Dioxoaanes

Journal of the American Chemical Society

Volumn 92, Issue 18, 1970, Pages 5394-5402

  Willy, W Edward ^a   Binsch, Gerhard ^a   Eliel, Ernest L ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000513361     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00721a018     Document Type: Article

References (88)

1. Paper XXI: F. W. Nader and E. L. Eliel, J. Amer. Chem. Soc., 92, 3050 (1970).
2. From the Ph.D. Dissertation of W. E. Willy, University of Notre Dame, Notre Dame, Ind., 1969 Preliminary publication: Tetrahedron Lett., 1775 (1969).
3. For comprehensive reviews, see (a) E. L. Eliel, “Stereochemistry of Carbon Compounds,” McGraw-Hill, New York, N. Y., 1962.
4. E. L. Eliel, N. L. Allinger, S. J. Angyal, and G. A. Morrison, “Conformational Analysis,” Wiley-Interscience, New York, N. Y., 1965.
5. M. Hanack, “Conformation Theory,” Academic Press, New York, N. Y., 1965.
6. J. McKenna, “Conformational Analysis of Organic Compounds,” The Royal Institute of Chemistry Lecture Series, No. 1, London, 1966.
7. for reviews of conformational analysis in heterocyclic systems, see F. G. Riddell, Quart. Rev. Chem. Soc., 21, 364 (1967).
8. E. L. Eliel, Kern. Tidskr., 81 (No. 6/7), 22 (1969).
9. C. Romers, C. Altona, H. R. Buys, and E. Havinga, Top. Stereochem., 4, 39 (1969).
10. E. L. Eliel, Accounts Chem. Res., 3, 1 (1970).
11. J. G. Aston, S. C. Schumann, H. L. Fink, and P. M. Doty, J. Amer. Chem. Soc., 63, 2029 (1941).
12. J. G. Aston, H. L. Fink, and S. C. Schumann, J. Amer. Chem. Soc., 65, 341 (1943).
13. J. E. Kilpatrick, K. S. Pitzer, and R. Spitzer, J. Amer. Chem. Soc., 69, 2483 (1947).
14. J. P. McCullough, R. E. Pennington, J. C. Smith, I. A. Hossenlopp, and G. Waddington, J. Amer. Chem. Soc., 81, 5880 (1959).
15. J. P. McCullough, J. Chem. Phys., 29, 966 (1958).
16. K. S. Pitzer and W. E. Donath, J. Amer. Chem. Soc., 81, 3213 (1959).
17. J. A. Greenhouse and H. L. Strauss, J. Chem. Phys., 50, 124 (1969).
18. F. V. Brutcher, Jr., and W. Bauer, Jr., J. Amer. Chem. Soc., 84, 2233 (1962).
19. F. V. Brutcher, Jr., T. Roberts, S. J. Barr, and N. Pearson, J. Amer. Chem. Soc., 81, 4915 (1959).
20. J. N. Haresnape, Chem. Ind. (London), 1091 (1953).
21. S. F. Birch and R. A. Dean, J. Chem. Soc., 2477 (1953).
22. M. B. Epstein, G. M. Barrow, K. S. Pitzer, and F. D. Rossini, J. Res. Nat. Bur. Stand., 43, 245 (1949).
23. C. Ouannes and J. Jacques, Bull. Soc. Chim. Fr., 3601 (1965).
24. A. Kankaanpera, Ph.D. Thesis, University of Turku, Turku, Finland, 1966.
25. R. U. Lemieux, J. D. Stevens, and R. R. Fraser, Can. J. Chem., 40, 1955 (1962).
26. M. Anteunis and F. Alderweireldt, Bull. Soc. Chim. Belg. 73, 889 (1964).
27. F. Alderweireldt and M. Anteunis, Bull. Soc. Chim. Belg., 74, 488 (1965).
28. C. Altona and A. P. M. van der Veek, Tetrahedron, 24, 4377 (1968).
29. J. B. Hendrickson, J. Amer. Chem. Soc., 83, 4537 (1961).
30. J. P. McCullough, D. R. Douslin, W. N. Hubbard, S. S. Todd, J. F. Messerly, I. A. Hossenlopp, F. R. Frow, J. P. Dawson, and G. Waddington, J. Amer. Chem. Soc., 81, 5884 (1959).
31. C. Altona, H. R. Buys, and E. Havinga, Recl. Trac. Chim. Pays-Bas, 85, 973 (1966).
32. M. Anteunis and F. Alderweireldt, Bull. Soc. Chim. Belg., 73, 903 (1964).
33. R. U. Lemieux, Can. J. Chem., 39, 116 (1961).
34. C. D. Jardetzky, J. Amer. Chem. Soc., 84, 62 (1962).
35. J. Amer. Chem. Soc., 83, 2919 (1961).
36. B. Post, R. S. Schwartz, and I. Fankuchen, J. Amer. Chem. Soc., 73, 5113 (1951).
37. S. Furberg and O. Hassel, Acta Chem. Scand., 4, 1584 (1950).
38. C. Altona, H. J. Geise, and C. Romers, Tetrahedron, 24, 13 (1968).
39. C. A. Beevers and W. Cochran, Proc. Roy. Soc., Ser. A., 190, 257 (1947).
40. D. Crowfoot, Annu. Rev. Biochem., 17, 134 (1948).
41. S. Furberg, Acta Chem. Scand., 4, 751 (1950).
42. M. Huber, Acta Crystallogr., 10, 129 (1957).
43. S. Furberg, Acta Chem. Scand., 14, 189 (1960).
44. E. Alver and S. Furberg, Acta Chem. Scand., 13, 910 (1959).
45. A summary of this subject is given in the Ph.D. Thesis of H. R. Buys, Leiden, The Netherlands, 1968.
46. H. R. Buys, C. Altona, and E. Havinga, Tetrahedron, 24, 3019 (1968).
47. R. G. Haber and B. Fuchs, Tetrahedron Lett., 1447 (1966).
48. N. Baggett, K. W. Buck, A. B. Foster, M. H. Randall, and J. M. Webber, J. Chem. Soc., 3394 (1965).
49. D. J. Triggle and B. Belleau, Can. J. Chem., 40, 1201 (1962).
50. B. E. Leggetter and R. K. Brown, Can. J. Chem., 43, 1030 (1965).
51. J.-C. Richer and C. Gilardeau, Can. J. Chem., 43, 3419 (1965).
52. E. L. Eliel and M. C. Knoeber, J. Amer. Chem. Soc., 90, 3444 (1968).
53. After this paper was submitted, a publication appeared reporting application of this technique to certain 2,4-disubstituted 1,3-dioxolanes: Y. Rommelaere and M. Anteunis, Bull. Soc. Chim. Belg., 79, 11 (1970).
54. P. Salomaa and A. Kankaanpera, Acta Chem. Scand., 15, 871 (1961).
55. S. A. Barker, E. J. Bourne, R. M. Pinkard, M. Stacey, and D. H. Whiffen, J. Chem. Soc., 3232 (1958).
56. N. Baggett, J. M. Duxbury, A. B. Foster, and J. M. Webber, J. Chem. Soc., C, 208 (1966).
57. J. S. Josan and F. W. Eastwood, Aust. J. Chem., 21, 2013 (1968).
58. H. J. Lucas and M. S. Guthrie, J. Amer. Chem. Soc., 72, 5490 (1950).
59. R. R. Fraser, R. U. Lemieux, and J. D. Stevens, J. Amer. Chem. Soc., 83, 3901 (1961).
60. J. Chuche, G. Dana, and M.-R. Monot, Bull. Soc. Chim. Fr., 3300 (1967).
61. D. Gagnaire and J.-B. Robert, Bull. Soc. Chim. Fr., 3646 (1965).
62. C. Altona, H. R. Buys, H. J. Hageman, and E. Havinga, Tetrahedron, 23, 2265 (1967).
63. F. A. L. Anet, J. Amer. Chem. Soc., 84, 747 (1962).
64. R. U. Lemieux in “Molecular Rearrangements,” P. deMayo, Ed., Wiley-Interscience, New York, N. Y., 1964, p 728.
65. P. Salomaa, Ann. Univ, Turku, Ser. A, 46 (1961).
66. Regarding the use of r (Beilstein nomenclature) see E. L. Eliel and F. W. Nader, J. Amer. Chem. Soc., 92, 584 (1970). See also International Union of Pure and Applied Chemistry, Information Bulletin No. 35, June 1969.
67. S. L. T. Thuan and J. Wiemann, Bull. Soc. Chim. Fr., 4550 (1968).
68. 48 using 70 % phosphoric acid as the reaction medium. Repetition of one of the preparations (2,r-4,cis-5-tri-i-Pr-1,3-dioxolane) in this study essentially confirmed the report (92 % of the syn and 8 % of the anti isomer was obtained). The reasoss for the high stereoselectivity in these largely kinetically controlled reactions are not clear D. R. Garrison, M. May, H. F. Ridley, and D. J. Triggle (J. Med. Chem., 12, 130 (1969)) report preparation ratios of 4:1 (syn:anti) and 3:1 (cis:trans) for diastereoisomeric mixtures of 2-methyl-4-cis-5-chloromethyl- and 2-methyl-4-(methyl-cis-chloromethyl)-1,3-dioxolane, respectively.
69. The calculation of specific torsional angles from coupling constants in five-membered rings is probably a dangerous procedure. It has been pointed out by V. Tabacik (Tetrahedron Lett., 555, 561 (1968)) that coupling constants should properly be integrated over the whole rotation circuit of conformationally mobile molecules rather than just summed over the most stable conformations. In five-membered rings where the energy wells are not so deep and pseudorotation or pseudo-libration may lead to rather wide conformational circuits, Tabacik's objection should be particularly pertinent and the classical procedure of assuming that the averaging of one, two, or three conformations with their appropriate torsional angles can be made to explain the observed coupling constants may be quite bad.
70. These couplings were determined from the ABX spectra of the molecules containing carbon-13 nuclei (natural abundance); see, for example, N. Sheppard and J. J. Turner, Proc. Roy. Soc., 252, 506 (1959).
71. M. Barfield, J. Chem. Phys., 41, 3825 (1964).
72. See J. C. Jochims and G. Taigel, Chem. Ber., 103, 448 (1970), for a case related to the present one.
73. The referee has drawn our attention to a previously reported case of a “stiff” furanose ring fused to a 1,4-dioxane ring in which two adjacent tranr-hydroxyl groups are fixed at a dihedral angle of about 150° to such a degree that periodate cleavage becomes very slow: R. U. Lemieux and R. Nagarajan, Can. J. Chem., 42, 1270 (1964).
74. J. Reisse, L. Nagels, and G. Chiurdoglu, Bull. Soc. Chim. Belg., 74, 162 (1965).
75. See, however, I. O. C. Ekejiuba and H. A. Hallam, Spectrochim. Acta, Part A, 26, 59, 67 (1970).
76. see, also, J. Chem. Soc., B, 209 (1970).
77. A. Brandstrom, Acta Chem. Scand., 13, 611 (1959).
78. R. Criegee, E. Höger, G. Huber, P. Kruck, F. Marktscheffel, and H. Schellenberger, Ann. Chem., 599, 81 (1956).
79. M. B. Green and W. J. Hickinbottom, J. Chem. Soc., 3262 (1957).
80. R. Kuhn and O. Rebel, Chem. Ber., 60, 1565 (1927).
81. G. Leuschner and K. Pfordte, Ann. Chem., 619, 1 (1958).
82. L. P. Kuhn, J. Amer. Chem. Soc., 80, 5950 (1958).
83. M. S. Newman and A. Arkell, J. Org. Chem., 24, 385 (1959).
84. J. Dale, J. Chem. Soc., 910 (1961).
85. R. Criegee and G. Schroder, Chem. Ber., 93, 689 (1960).
86. S. Winstein and L. Goodman, J. Amer. Chem. Soc., 76, 4368 (1954).
87. H. Hibbert and S. Hill, J. Amer. Chem. Soc., 45, 734 (1923).
88. K. W. Buck, F. A. Fahim, A. B. Foster, A. R. Perry, M. H. Qadir, and J. M. Webber, Carbohyd. Res., 2, 14 (1966).