Spheri city beyond topicity in characterizing stereochemical phenomena. Novel concepts based on coset representations and their subductions

Bulletin of the Chemical Society of Japan

Volumn 75, Issue 9, 2002, Pages 1863-1883

  Fujita, Shinsaku ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; DERIVATIVES; ETHANE; METHANE; MOLECULAR ORIENTATION;

COSET REPRESENTATIONS (CR); SPHERICITY;

STEREOCHEMISTRY;

BIPHENYL DERIVATIVE; ETHANE; FERROCENE; LIGAND; METHANE;

ARTICLE; ATOM; CHIRALITY; COMBINATORIAL CHEMISTRY; STEREOCHEMISTRY;

EID: 0036393602     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.75.1863     Document Type: Article

References (157)

1. J. H. van't Hoff, Arch. Neerl. Sci. Exactes Nat., 9, 445 (1874).
2. A. Werner, Anorg. Chem., 3, 267 (1893).
3. A.M. Rouhi, Chem. Eng. News, (Sept. 6), 28 (1999).
4. E. Eliel and S. H. Wilen, "Stereochemistry of Organic Compounds," John Wiley & Sons, New York (1994).
5. A. von Zelewsky, "Stereochemistry of Coordination Compounds," John Wiley & Sons, Chichester (1996).
6. F. M. Jaeger, "Spacial Arrangements of Atomic Systems and Optical Activity," McGraw-Hill, New York (1930).
7. J. K. O'Loane, Chem. Rev., 80, 41 (1980).
8. R. S. Cahn, C. K. Ingold, and V. Prelog, Angew. Chem., Int. Ed. Engl., 5, 385 (1966).
9. K. R. Hanson, J. Am. Chem. Soc., 88, 2731 (1966).
10. H. Hirschmann and K. R. Hanson, Eur. J. Biochem., 22, 301 (1971).
11. H. Hirschmann and K. R. Hanson, J. Org. Chem., 36, 3293 (1971).
12. V. Prelog, Chem. Brit., 4, 382 (1968).
13. V. Prelog and G. Helmchen, Helv. Chim. Acta, 55, 2581 (1972).
14. V. Prelog, Science, 193, 17 (1976).
15. H. Hirschmann and K. R. Hanson, Tetrahedron, 30, 3649 (1974).
16. H. Hirschmann, Trans. N. Y. Acad. Sci. Ser. II, 41, 61 (1983).
17. H. Hirschmann and K. R. Hanson, Top. Stereochem., 14, 183 (1983).
18. K. Mislow and M. Raban, Top. Stereochem., 1, 1 (1967).
19. M. Nakazaki, Kagaku (Kyoto), 23, 614 (1968), in Japanese.
20. M. Nakazaki, Kagaku no Ryoiki (Tokyo), 22, 1057 (1968), in Japanese.
21. E. L. Eliel, J. Chem. Educ., 57, 52 (1980).
22. K. Mislow and J. Siegel, J. Am. Chem. Soc., 106, 3319 (1984).
23. R. L. Flurry, J. Am. Chem. Soc., 103, 2901 (1981).
24. J. A. Pople, J. Am. Chem. Soc., 102, 4615 (1980).
25. G.E. McCasland, "A New General System for the Naming of Stereoisomers," Chemical Astracts, Columbus (1953).
26. V. Prelog and G. Helmchen, Angew. Chem., Int. Ed. Engl., 21, 567-583 (1982).
27. E. L. Eliel, Top. Curr. Chem., 105, 1 (1982).
28. P. Mata, A. M. Lobo, C. Marshall, and A. P. Johnson, Tetrahedron: Asymmetry, 4, 657 (1993).
29. M. Perdih and M. Razinger, Tetrahedron: Asymmetry, 5, 835 (1994).
30. P. Mata and R. B. Nachbar, Tetrahedron: Asymmetry, 6, 693 (1995).
31. R. M. Silverstein, G. C. Bassler, and T.C. Morrill, "Infrared and Raman Spectra of Polyatomic Molecules," Van Nostrand, New York (1945).
32. W. B. Jenning, Chem. Rev., 75, 307 (1975).
33. R. M. Silverstein, G. C. Bassler, and T. C. Morrill, "Spectroscopic Identification of Organic Compounds," 4th ed, John & Wiley, New York (1981).
34. G. Binsch, E. L. Eliel, and H. Kessler, Angew. Chem., Int. Ed. Engl., 10, 570 (1971).
35. H. H. Jaffé and M. Orchin, "Symmetry in Chemistry," Wiley, Chichester (1965).
36. L. H. Hall, "Group Theory and Symmetry in Chemistry," McGraw-Hill, New York (1969).
37. F. A. Cotton, "Chemical Applications of Group Theory," Wiley-International, New York (1971).
38. D. M. Bishop, "Group Theory and Chemistry," Clarendon, Oxford (1973).
39. I. Hargittai and H. Hargittai, "Symmetry through the Eyes of a Chemist," VCH, Weinheim (1986).
40. E. L. Eliel, N. L. Allinger, S. J. Angyal, and G. A. Morrison, "The Conformational Analysis," John-Wiley & Sons, New York (1965).
41. J. B. Lambert and S. I. Featherman, Chem. Rev., 75, 611 (1975).
42. R. A. Newmark and C. H. Sederholm, J. Chem. Phys., 63, 602 (1965).
43. M. Nakamura, M. Oki, and H. Nakanishi, J. Am. Chem. Soc., 95, 7169 (1973).
44. K. Schlögel, Top. Stereochem., 1, 39 (1967).
45. K. Mislow, Science, 120, 232 (1954).
46. K. Mislow and R. Bolstad, J. Am. Chem. Soc., 77, 6712 (1955).
47. P. Finocchiaro, D. Gust, and K. Mislow, J. Am. Chem. Soc., 96, 3198 (1974).
48. E. L. Eliel, Israel J. Chem., 15, 7 (1976/1977).
49. E. Ruch, Acc. Chem. Res., 5, 49 (1972).
50. E. Ruch, Angew. Chem., Int. Ed. Engl., 16, 65 (1977).
51. C. A. Mead, Top. Curr. Chem., 49, 1 (1974).
52. I. Ugi, D. Marquading, H. Klusacek, G. Gokel, and P. Gillespie, Angew. Chem., Int. Ed., 9, 703 (1970).
53. I. Ugi, J. Dugundji, R. Kopp, and D. Marquarding, "Perspectives in Theoretical Stereochemistry," Springer-Verlag, Berlin-Heidelberg (1984).
54. I. Ugi, Chimia, 40, 340 (1986).
55. J. Brocas, M. Gielen, and R. Willem, "The Permutational Approach to Dynamic Stereochemistry," McGraw-Hill International, New York (1983).
56. "The Permutation Group in Physics and Chemistry (Lecture Notes in Chemistry 12)," ed by J. Hinze, Springer-Verlag, Berlin Heidelberg (1979).
57. J. G. Nourse, J. Am. Chem. Soc., 101, 1210 (1979).
58. G. Pólya, Compt. Rend., 201, 1167 (1935).
59. G. Pólya, Helv. Chim. Acta, 19, 22 (1936).
60. G. Pólya, Z. Kristal. (A), 93, 415 (1936).
61. G. Pólya, Acta Math., 68, 145 (1937).
62. N. G. de Bruijn, Indag. Math., 21, 59 (1959).
63. J. H. Redfield, Amer. J. Math., 49,433 (1927).
64. J. H. Redfield, J. Graph Theory, 8, 205 (1984).
65. R. A. Davidson, J. Amer. Chem. Soc., 103, 312 (1981).
66. R. C. Read, J. London Math. Soc., 34, 417 (1959).
67. R. C. Read, J. London Math. Soc., 35, 344 (1960).
68. R. C. Read, Canad. J. Math., 20, 808 (1968).
69. D. H. Rouvray, Chem. Soc. Rev., 3, 355 (1974).
70. F. Harary, E. M. Palmer, R. W. Robinson, and R. C. Read, in "Chemical Aplications of Graph Theorey," ed by A. T. Balaban, Academic, London (1976), pp. 11-24.
71. K. Balasubramanian, Chem. Rev., 85, 599 (1985).
72. "Chemical Applications of Graph Theory," ed by A. T. Balaban, Academic Press, London (1976).
73. G. Pólya, R. E. Tarjan, and D. R. Woods, "Notes on Introductory Combinatorics," Birkhäuser, Boston (1983).
74. G. Pólya and R. C. Read, "Combinatorial Enumeration of Groups, Graphs, and Chemical Compounds," Springer-Verlag, New York (1987).
75. E. Ruch, W. Hässelbarth, and B. Richter, Theor. Chim. Acta, 19, 288 (1970).
76. E. Ruch and D. J. Klein, Theor. Chim. Acta, 63, 447 (1983).
77. W. J. Taylor, J. Chem. Phys., 11, 532 (1943).
78. T. L. Hill, J. Chem. Phys., 11, 294 (1943).
79. D. H. McDaniel, Inorg. Chem., 11, 2678 (1972).
80. J. E. Leonard, J. Phys. Chem., 81, 2212 (1977).
81. J. R. L. Flurry, J. Chem. Educ., 61, 663 (1984).
82. J. Sheehan, Canad. J. Math., 20, 1068 (1968).
83. A. Kerber and K.-J. Thürlings, in "Combinatorial Theory," ed by D. Jngnickel and K. Vedder, Springer, Berlin (1982), pp. 191-211.
84. W. Häisselbarth, Theor. Chim. Acta, 67, 339 (1985).
85. J. Brocas, J. Am. Chem. Soc., 108, 1135 (1986).
86. C. A. Mead, J. Am. Chem. Soc., 109, 2130 (1987).
87. E. K. Lloyd, J. Math. Chem., 11, 207 (1992).
88. S. Fujita, "Symmetry and Combinatorial Enumeration in Chemistry," Springer-Verlag, Berlin-Heidelberg (1991).
89. S. Fujita, J. Am. Chem. Soc., 112, 3390 (1990).
90. W. Burnside, "Theory of Groups of Finite Order," 2nd ed, Cambridge University Press, Cambridge (1911).
91. S. Fujita, Theor. Chim. Acta, 76, 247 (1989).
92. S. Fujita, Bull. Chem. Soc. Jpn., 63, 315 (1990).
93. S. Fujita, Memoirs of the Faculty of Engineering and Design, Kyoto Institute of Technology, 47, 111 (1999).
94. H. B. Kagan, "La Stéréochimie Organique," Presses Universitaires de France (1975).
95. S. F. A. Kettle, "Symmetry and Structure," Wiley, Chichester (1985).
96. D. C. Harris and M. D. Bertolucci, "Symmetry and Spectroscopy," Dover, New York (1989).
97. M. F. C. Ladd, "Symmetry in Molecules and Crystals," Ellis Horwood, Chichester (1989).
98. K. Mislow, Bull. Soc. Chim. Belg., 86, 595 (1977).
99. S. Fujita, Bull. Chem. Soc. Jpn., 73, 1979 (2000).
100. The Commission on the Nomenclature of Organic Chemistry of IUPAC, Pure Appl. Chem., 45, 11 (1976).
101. S. Fujita,J. Chem. Inf. Comput. Sci., 32, 354 (1992).
102. S. Fujita, Tetrahedron, 56, 735 (2000).
103. 9 is replaced by the term prostereogenic center. The terms "prochiral centers" and "propseudoasymmetric centers", 3 are replaced by the term prostereogenic center.
104. 13 are replaced by the term stereogenic center.
105. S. Fujita, Tetrahedron, 46, 5943 (1990).
106. S. Fujita, J. Chem. Inf. Comput. Sci., 31, 540 (1991).
107. S. Fujita, Bull. Chem. Soc. Jpn., 63, 2770 (1990).
108. S. Fujita, Bull. Chem. Soc. Jpn., 63, 1876 (1990).
109. S. Fujita, Bull. Chem. Soc. Jpn., 63, 203 (1990).
110. S. Fujita,J. Chem. Inf. Comput. Sci., 39, 151 (1999).
111. S. Fujita, Polyhedron, 12, 95 (1993).
112. S. Fujita, Bull. Chem. Soc. Jpn., 63, 2759 (1990).
113. S. Fujita, Bull. Chem. Soc. Jpn., 64, 3215 (1991).
114. S. Fujita, Tetrahedron, 47, 31 (1991).
115. S. Fujita, Bull. Chem. Soc. Jpn., 73, 2679 (2000).
116. S. Fujita, Bull. Chem. Soc. Jpn., 74, 1015 (2001).
117. S. Fujita, Bull. Chem. Soc. Jpn., 73, 2009 (2000).
118. For Erratum for S. Fujita, Bull. Chem. Soc. Jpn., 73, 2009 (2000), see Bull. Chem. Soc. Jpn., 74, 1163 (2001).
119. S. Fujita, Tetrahedron, 46, 365 (1990).
120. S. Fujita, J. Chem. Inf. Comput. Sci., 36, 270 (1996).
121. M. Nakazaki, "Bunshi no Katachi to Taisho-Sono Hyoji Hou," Nankodo, Tokyo (1969).
122. 2′.
123. D. Walba, in "Chemical Applications of Topology and Graph Theory," ed by R. B. King, Elsevier, Amsterdam (1983), Vol. 28 of Studies in Physical and Theoretical Chemistry, pp. 17-32.
124. E. Flapan, "When Topology Meets Chemistry. A Topological Look at Molecular Chirality," Cambridge Univ. Press, Cambride (2000), pp. 19-21 and pp. 110-111.
125. S. Fujita,J. Chem. Inf. Comput. Sci., 40, 135 (2000).
126. M. G. Hutchings, J. D. Andose, and K. Mislow, J. Am. Chem. Soc., 97, 4553 (1975).
127. M. Nakazaki, K. Naemura, and Y. Hokura, J. Chem. Soc., Chem. Commun., 1982, 1245.
128. G. E. McCasland, R. Horvat, and M. R. Roth, J. Am. Chem. Soc., 81, 2399 (1959).
129. S. Fujita,J. Chem. Inf. Comput. Sci., 40, 426 (2000).
130. S. Fujita, Bull. Chem. Soc. Jpn., 72, 2409 (1999).
131. S. Fujita, Theor. Chim. Acta, 78, 45 (1990).
132. S. Fujita, J. Math. Chem., 12, 173 (1993).
133. S. Fujita, Theor. Chim. Acta, 82, 473 (1992).
134. S. Fujita, J. Math. Chem., 5, 99 (1990).
135. S. Fujita, J. Math. Chem., 5, 121 (1990).
136. S. Fujita, Bull. Chem. Soc. Jpn., 62, 3771 (1989).
137. S. Fujita, Theor. Chim. Acta, 77, 307 (1990).
138. S. Fujita, Bull. Chem. Soc. Jpn., 63, 2033 (1990).
139. S. Fujita, J. Graph Theory, 18, 349 (1994).
140. S. Fujita, Theor. Chem. Acta, 91, 291 (1995).
141. S. Fujita, Theor. Chem. Acta, 91, 315 (1995).
142. S. Fujita, Theor. Chem. Acc., 99, 224 (1998).
143. S. Fujita, Bull. Chem. Soc. Jpn., 71, 1587 (1998).
144. S. Fujita, Bull. Chem. Soc. Jpn., 71, 2071 (1998).
145. S. Fujita, Bull. Chem. Soc. Jpn., 71, 2309 (1998).
146. S. Fujita, Theor. Chem. Acc., 99, 404 (1998).
147. S. Fujita, Theor. Chem. Acc., 101, 409 (1999).
148. S. Fujita, Bull. Chem. Soc. Jpn., 72, 13 (1999).
149. S. Fujita, Bull. Chem. Soc. Jpn., 72, 2403 (1999).
150. S. Fujita,J. Chem. Inf. Comput. Sci., 40, 1101 (2000).
151. S. Fujita, Bull. Chem. Soc. Jpn., 67, 2935 (1994).
152. S. Fujita, Bull. Chem. Soc. Jpn., 67, 2927 (1994).
153. S. Fujita, J. Chem. Soc., Faraday Trans., 94, 2515 (1998).
154. S. Fujita,J. Chem. Inf. Comput. Sci., 38, 876 (1998).
155. S. Fujita, J. Chem. Soc., Faraday Trans., 94, 3197 (1998).
156. S. Fujita, Bull. Chem. Soc. Jpn., 72, 1759 (1999).
157. S. Fujita, unpublished data.