Conformations, chiroptical and related spectral properties of enones

The Chemistry of the Metal Carbon Bond, Carbon-Carbon Bond Formation Using Organometallic Compounds

Volumn , Issue , 2010, Pages 55-105

  Gawronski, Jacek ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Cyclohexenones; Infrared spectroscopy; Polyenones; Pyramidalization; Transitions

Indexed keywords

ELECTRON TRANSITIONS; INFRARED SPECTROSCOPY;

CYCLOHEXENONES; POLYENONES; PYRAMIDALIZATION; SPECTRAL PROPERTIES;

KETONES;

EID: 84948742711     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470772218.ch3     Document Type: Chapter

References (163)

1. R. J. Loncharich, T. R. Schwartz and K. N. Houk, J. Am. Chem. Soc, 109, 14 (1987).
2. S. Marriott and R. D. Topsom, J. Mol. Struct., 106, 277 (1984).
3. C. E. Blom, G. Grassi and A. Bauer, J. Am. Chem. Soc, 106, 7427 (1984).
4. E. A. Cherniak and C. C. Costain, J. Chem. Phys., 45, 104 (1966).
5. T. Liljefors and N. L. Allinger, J. Am. Chem. Soc, 98, 2745 (1976).
6. J. K. Gawronski and H. M. Walborsky, J. Org. Chem., 51, 2863 (1986).
7. H. O. House, in Stereochemistry and Reactivity of Systems Containing n Electrons (Ed. W. H. Watson), Verlag Chemie Int., Deerfield Beach, 1983, pp. 279-317.
8. E. A. Braude and C. J. Timmons, J. Chem. Soc, 3766 (1955).
9. F. H. Cottee, B. P. Straugham, C. J. Timmons, W. F. Forbes and R. Shilton, J. Chem. Soc. (B), 1146(1967).
10. K. Noack, Spectrochim. Acta, 18, 1625 (1962).
11. H.-J. Oelichmann, D. Bougeard and B. Schrader, J. Mol. Struct., 77,179 (1981); 77,149 (1981).
12. H. N. A. Al-Jallo and E. S. Waight, J. Chem. Soc. (B), 73 (1966); 75 (1966).
13. R. L. Erskine and E. S. Waight, J. Chem. Soc, 3425 (1960).
14. K. Noack and R. N. Jones, Can. J. Chem., 39, 2201 (1961).
15. J. G. Angyan, A. Kucsman, R. A. Poirier and I. G. Csizmadia, J. Mol. Struct. {Theochem), 123, 189 (1985).
16. F. S. Jorgensen, L. Carlsen and F. Duus, J. Am. Chem. Soc, 103, 1350 (1981).
17. H. Martens, G. Hoornaert and S. Toppet, Tetrahedron, 29, 4241 (1973).
18. H. Dodziuk, K. Kamienska-Trela and J. Dabrowski, Roczniki Chem., 44, 393 (1970).
19. A. R. Katritzky, R. F. Pinzelli and R. D. Topsora, Tetrahedron, 28, 3449 (1972).
20. R. Mecke and K. Noack, Chem. Ber., 93, 210 (1960).
21. E. S. Waight and R. L. Erskine, in Steric Effects in Conjugated Systems (Ed. G. W. Gray), Butterworths, London, 1958, pp. 73-81.
22. A. Bienvenue, J. Am. Chem. Soc, 95, 7345 (1973).
23. A. Bienvenue and B. Duchatellier, Tetrahedron, 28, 833 (1972).
24. W. P. Hayes and C. J. Timmons, Spectrochim. Acta, 24A, 323 (1968).
25. C. E. Blom, R. P. Miiller and H. H. Gunthard, Chem. Phys. Lett., 73, 483 (1980).
26. K. Noack and R. N. Jones, Can. J. Chem., 39, 2225 (1961).
27. A. J. Bowles, W. O. George and W. F. Maddams, J. Chem. Soc. (B), 810 (1969).
28. A. F. Kluge and C. P. Lillya, J. Org. Chem., 36, 1977 (1971).
29. H.-J. Oelichmann, D. Bougeard and B. Schrader, Angew. Chem., Int. Ed. Engl., 21, 639 (1982).
30. H. Junge, Spectrochim. Acta, 24A, 1965 (1968).
31. J. Dabrowski and K. Kamienska-Trela, Bull. Chem. Soc. Jpn., 39, 2565 (1966).
32. J. Dabrowski and M. Tencer, Bull. Chem. Soc. Jpn., 48, 1310 (1975).
33. J. Dabrowski and K. Kamienska-Trela, Spectrochim. Acta, 22, 211 (1966).
34. W. R. Benson and A. E. Pohland, J. Org. Chem., 29, 385 (1964).
35. L. Kania, K. Kamienska-Trela and M. Witanowski, J. Mol. Struct., 102, 1 (1983).
36. D. Smith and P. J. Taylor, Spectrochim. Acta, 32A, 1477 (1976).
37. D. W. Boerth, J. Org. Chem., 47, 4085 (1982) and references cited therein.
38. C. F. Dykstra, J. Am. Chem. Soc, 98, 7182 (1976).
39. E. R. Davidson and L. E. Nitzsche, J. Am. Chem. Soc, 101, 6524 (1979).
40. J. C. D. Brand and D. G. Williamson, Discuss. Faraday Soc, 35, 184 (1963).
41. R. C. Cookson and S. H. Dandegaonker, J. Chem. Soc, 1651 (1955).
42. M. F. Nicol, Appl. Spectrosc. Rev., 8, 183 (1974).
43. S. Iwata and K. Morokuma, J. Am. Chem. Soc, 97, 966 (1975).
44. R. B. Woodward, J. Am. Chem. Soc, 63, 1123 (1941); 64, 76 (1942).
45. J. M. Hollas, Spectrochim. Acta, 19, 1425 (1963).
46. W. F. Forbes and R. Shilton, J. Am. Chem. Soc, 81, 786 (1959).
47. H. O. House and R. S. Ro, J. Am. Chem. Soc, 80, 2428 (1958).
48. P. K. Das and R. S. Becker, J. Phys. Chem., 82, 2081 (1978).
49. T. Takemura, P. K. Das, G. Hug and R. S. Becker, J. Am. Chem. Soc, 98, 7099 (1976).
50. L. F. Fieser and M. Fieser, Steroids, Van Nostrand-Reinhold, Princeton, 1959, pp. 15-21.
51. T. Liljefors and N. L. Allinger, J. Am. Chem. Soc, 100, 1068 (1978).
52. E. A. Braude and C. J. Timmons, J. Chem. Soc, 3766 (1955).
53. E. A. Braude and F. Sondheimer, J. Chem. Soc, 3754 (1955).
54. D. A. Lightner, M. J. Flores, B. V. Crist and J. K. Gawronski, J. Org. Chem., 45, 3518 (1980).
55. A. F. Cameron and G. Jamieson, J. Chem. Soc. (B), 1581 (1971).
56. H. O. House, R. F. Sieloff, T. V. Lee and M. B. De Tar, J. Org. Chem., 45, 1800 (1980).
57. W. E. Thiessen, H. A. Levy, W. G. Dauben, G. H. Beasley and D. A. Cox, J. Am. Chem. Soc, 93, 4312 (1971).
58. J. Dabrowski and K. Kamienska-Trela, J. Am. Chem. Soc, 98, 2826 (1976).
59. C. Skbtsch and E. Breitmaier, Chem. Ber., 113, 795 (1980).
60. J. Dabrowski and M. Tencer, Tetrahedron, 32, 587 (1976).
61. L. Bardon, J. Elquero and R. Jacquier, Bull. Soc. Chim. France, 297 (1967).
62. G. Quinkert, G. Durner, E. Kleiner, F. Adam, E. Haupt and D. Leibfritz, Chem. Ber., 113,2227 (1980).
63. N. Boccara and P. Maitte, Tetrahedron Lett., 4031 (1977).
64. W. K. Chan, K. Nakanishi, T. G. Ebrey and B. Honig, J. Am. Chem. Soc, 96, 3642 (1974).
65. R. Gilardi, I. L. Karle, J. Karle and W. Sperling, Nature, 232, 187 (1971).
66. R. Gilardi, I. L. Karle and J. Karle, Acta Crystallogr., Sect. B, 28, 2605 (1972).
67. T. Hamanaka, T. Mitsui and M. Kakudo, Acta Crystallogr., Sect. B, 28, 214 (1972).
68. A. Warshel and M. Karplus, J. Am. Chem. Soc, 96, 5677 (1974).
69. I. Naito, A. Kinoshita and T. Yonemitsu, Bull. Chem. Soc. Jpn., 49, 339 (1976).
70. J. E. Baldwin, J. Org. Chem., 30, 2423 (1965).
71. D. D. Faulk and A. Fry, J. Org. Chem., 35, 364 (1970).
72. C. J. Timmons, Chem. Commun., 576 (1965).
73. F. H. Cottee and C. J. Timmons, J. Chem. Soc. (B), 326 (1968).
74. D. H. Williams, Tetrahedron Lett., 2305 (1965).
75. P. Bass and H. Cerfontain, Tetrahedron, 33, 1509 (1977).
76. J. Ronayne, M. V. Sargent and D. H. Williams, J. Am. Chem. Soc, 88, 5288 (1966).
77. G. Montaudo, V. Librando, S. Caccamese and P. Maravigna, J. Am. Chem. Soc, 95,6365 (1973).
78. T. M. Filippova, A. R. Bekker and B. D. Lavrukhin, Org. Magn. Reson., 14, 337 (1980).
79. J. Dabrowski and L. J. Kozerski, Org. Magn. Reson., 4, 137 (1972).
80. T. Toda, M. C. Woods and K. Takahashi, Tetrahedron, 27, 5391 (1971).
81. K. Mullen, S. Bender, E. Kotzamani, H. Schmickler, B. Frei and H. R. Wolf, Tetrahedron Lett., 22, 3513 (1981).
82. M. L. Filleux-Blanchard, F. Mabon and C. J. Martin, Tetrahedron Lett., 3907 (1974).
83. M. Tencer and J. Dabrowski, Spectroscopy Lett., 16, 351 (1983).
84. D. H. Marr and J. B. Stothers, Can. J. Chem., 43, 596 (1965).
85. S. Braun, Org. Magn. Reson., 11, 197 (1978).
86. M. W. Barrett, R. D. Farrant, D. N. Kirk, J. D. Mersh, J. K. M. Sanders and W. L. Duax, J. Chem. Soc. Perkin Trans. 2, 105 (1982).
87. F. Pavelcik, K. Havetta and V. Suchy, Acta Crystallogr.. Sect. C, 41, 1272 (1985).
88. K.Tokuno,M.Matsui,F.Miyoshi,Y.Asao and T.Ohashi,ActaCrystallogr..Sect.C,42,85(1986).
89. D. Rabinovich, J. Chem. Soc. (B), 11 (1970).
90. S. K. Branch and I. W. Nowell, Acta Crystallogr.. Sect. C, 41, 769 (1985).
91. A. E. Jungk and G. M. J. Schmidt, J. Chem. Soc. (B), 1427 (1970).
92. A. Hoser, Z. Kajuski, H. Majuszynska and V. D. Orlov, Acta Crystallogr., Sect. B, 36, 1256 (1980).
93. Z. Kaluski, E. Skrzypczak-Jankun, V. D. Orlov and A. I. Borovoi, Bull. Acad. Pol. So'., Ser. Chim., 26, 869 (1978).
94. A. Katrusiak, M. Ratajczak-Sitarz, Z. Kaluski and V. D. Orlov, Acta Crystallogr.. Sect. C, 43, 103 (1987).
95. A. Katrusiak, M. Ratajczak-Sitarz, Z. Kaluski, V. D. Orlov, U. A. Borovoi and E. I. Mihedkina, Acta Crystallogr.. Sect. C, 43, 342 (1987).
96. V. Zabel, W. H. Watson, S. Alvarado, J. F. Ciccio and J. Calzada, Acta Crystallogr. Sect. B, 36, 2816 (1980).
97. Mazhar-Ul-Haque, D. Rogers and C. N. Caughlan, J. Chem. Soc. Perkin Trans. 2, 223 (1974).
98. M. J. Bovill, M. H. P. Guy, G. A. Sim, D. N. J. White and W. Herz, J. Chem. Soc. Perkin Trans. 2, 53 (1979).
99. M. Soriano-Garcia, B. Ortiz and R. A. Toscano, Acta Crystallogr., Sect. C, 40, 479 (1984).
100. W. L. Duax, C. Eger, S. Pokrywiecki and Y. Osawa, J. Med. Chem., 14, 295 (1971).
101. P. J. Cox and G. A. Sim, Acta Crystallogr., Sect. B, 38, 1360 (1982).
102. C. M. Weeks, W. L. Duax and Y. Osawa, Acta Crystallogr., Sect. B, 31, 1502 (1975).
103. A. Cooper, C. T. Lu and D. A. Norton, J. Chem. Soc. (B), 1228 (1968).
104. Atlas of Steroid Structure, Vol. 1 (Eds. W. L. Duax and D. A. Norton), IFI-Plenum, New York, 1975; Vol. 2 (Eds. J. F. Griffin, W. L. Duax and C. M. Weeks), IFI-Plenum, New York, 1984.
105. W. L. Duax, C. M. Weeks and D. C. Rohrer, Top. Stereochem., 9, 271 (1976).
106. C. Romers, C. Altona, H. J. C. Jacobs and R. A. G. de Graaf, Terpenoids and Steroids, 4, 531 (1974).
107. P. J. Roberts, J. C. Coppola, N. W. Isaacs and O. Kennard, J. Chem. Soc. Perkin Trans. 2, IIA (1973).
108. H. Campsteyn, L. Dupont and O. Dideberg, Acta Crystallogr.. Sect. B, 30, 90 (1974).
109. M. M. Bhadbhade and K. Venkatesan, Acta Crystallogr. Sect. C, 40, 1905 (1984).
110. G. Precigoux, B. Busetta, C. Courseille and M. Hospital, Acta Crystallogr.. Sect. B. 31, 1527 (1975).
111. W. L. Duax, V. Cody, J. F. Griffin, J. Hazel and C. M. Weeks, J. Steroid Biochem., 9, 901 (1978).
112. M. J. Begley, E. A. Frecknall and G. Pattenden, Acta Crystallogr.. Sect. C, 40, 1745 (1984).
113. H. Irngartinger, M. Nixdorf, W. Dobler and R. Gleiter, Acta Crystallogr., Sect. C, 40, 1481 (1984).
114. J. D. M. Asher and G. A. Sim, J. Chem. Soc, 6041 (1965).
115. D. N. J. White and G. A. Sim, J. Chem. Soc, Perkin Trans. 2, 1826 (1975).
116. A. T. McPhail and K. D. Onan, J. Chem. Soc, Perkin Trans. 2, 332 (1976).
117. B. Norden, Appl. Spectrosc. Rev., 14, 157 (1978).
118. J. Michl and E. W. Thulstrup, Spectroscopy with Polarized Light. Solute Alignment by Photoselection, in Liquid Crystals, Polymers, and Membranes, Verlag Chemie, New York, 1986.
119. A. Yogev, L. Margulies, D. Amar and Y. Mazur, J. Am. Chem. Soc, 91, 4558 (1969).
120. A. Yogev, J. Riboid, J. Marero and Y. Mazur, J. Am. Chem. Soc, 91 4559 (1969).
121. J. Gawronski, T. Liljefors and B. Norden, J. Am. Chem. Soc, 101, 5515 (1979).
122. L. Velluz, M. Legrand and M. Grosjean, Optical Circular Dichroism, Chapt. 4, Academic Press, New York, 1965.
123. G. Snatzke, in Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry (Ed. G. Snatzke), Chap. 13, Heyden, London, 1967.
124. G. Snatzke and F. Snatzke, in Fundamental Aspects and Recent Developments in Optical Rotatory Dispersion and Circular Dichroism (Eds. F. Ciardelli and P. Salvadori), Heyden. London, 1973, pp. 109-116., 121-123.
125. M. Legrand and M. J. Rougier, in Stereochemistry, Fundamentals and Methods, Vol. 2 (Ed. H. B. Kagan), G. Thieme, Stuttgart, 1977, pp. 123-127.
126. J. Gawronski, Tetrahedron, 38, 3 (1982).
127. D. N. Kirk, Tetrahedron, 42, 777 (1986).
128. C. Djerassi, R. Records, E. Bunnenberg, K. Mislow and A. Moscowitz, J. Am. Chem. Soc, 84,870 (1962).
129. W. B. Whalley, Chem. Ind., 1024 (1962).
130. W. Hug and G. Wagniere, Helv. Chim. Acta, 54, 633 (1971).
131. Kam-khow Cheong, A. Oshita, D. J. Caldwell and H. Eyring, Proc. Natl. Acad. Sei. U.S.A., 67, 1727 (1970); Topics Modern Phys., 93 (1971).
132. T. Aoyama and H. Yamakawa, Nippon Kagaku Kaishi, 1 (1976).
133. G. Snatzke, Tetrahedron, 21, 413 (1965).
134. G. Snatzke, Angew. Chem., Int. Ed. Engl., 18, 363 (1979).
135. G. Snatzke, in Optical Activity and Chira! Discrimination (Ed. S. F. Mason), D. Reidel, Dordrecht, 1979, pp. 53-54.
136. G. Snatzke, Tetrahedron, 21, 439 (1965).
137. M. Duraisamy and H. M. Walborsky, J. Am. Chem. Soc, 105, 3264 (1983).
138. F. Labruyere, C. Bertrand, C. Metge, A. Dubourg, R. Roques, J. P. Declercq and G. Germain, Acta Crystallogr., Sect. C, 40, 277 (1984).
139. G. Snatzke, Tetrahedron, 21, 421 (1965).
140. V. Delaroff, N. Dupuy, L. Nedelac and M. Legrand, Tetrahedron, 35, 2681 (1979).
141. T. Sato, M. Tada, T. Takahashi, I. Horibe, H. Ishii, T. Iwata, K. Kuriyama, Y. Tamura and K. Tori, Chem. Lett., 1191 (1977).
142. M. Tada, T. Sato, T. Takahashi, K. Tori, I. Horibe and K. Kuriyama, J. Chem. Soc. Perkin Trans. 1, 2695 (1981).
143. H. Ziffer and C. H. Robinson, Tetrahedron, 24, 5803 (1968).
144. A. W. Burgstahler and R. C. Barkhurst, J. Am. Chem. Soc, 92, 7601 (1970).
145. A. W. Burgstahler, R. C. Barkhurst and J. K. Gawronski, in Modern Methods of Steroid Analysis(Ed. E. Heftmann), Chap. 16, Academic Press, New York, 1973.
146. K. Kuriyama, M. Moriyama, T. Iwata and K. Tori, Tetrahedron Lett., 1661 (1968).
147. A. F. Beecham, Tetrahedron, 27, 5207 (1971).
148. R. N. Totty and J. Hudec, Chem. Commun., 785 (1971).
149. E. M. Gopalakrishna, A. Cooper and D. A. Norton, Acta Crystallogr., Sect. B, 25, 639 (1969).
150. L. Velluz, M. Legrand and R. Viennet, CR. Hebd. Seances Acad. Sei., 261, 1687 (1965).
151. R. D. Burnett and D. N. Kirk, J. Chem. Soc, Perkin Trans. 1, 1460 (1981).
152. W. Eschenmoser, P. Uebelhart and C. H. Eugster, Helv. Chim. Acta, 64, 2681 (1981).
153. R. Buchecker. P. Hamm and C. H. Eugster, Chimia, 25, 192 (1971).
154. H. Mayer and A. Ruettimann, Helv. Chim. Acta, 63, 1451 (1980).
155. M. Koreeda, G. Weiss and K. Nakanishi, J. Am. Chem. Soc, 95, 239 (1973).
156. N. Harada, J. Am. Chem. Soc, 95, 240 (1973).
157. M. Sumiyoshi, H. Kuritani and K. Shingu, Chem. Commun., 812 (1977).
158. S. F. Mason, J. Chem. Soc. (B), 370 (1966).
159. S. F. Mason, in Optica! Rotatory Dispersion and Circular Dichroism in Organic Chemistry (Ed. G. Snatzke), Heyden, London, 1967, p. 71.
160. N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley. 1983.
161. M. Koreeda, N. Harda and K. Nakanishi, J. Am. Chem. Soc, 96, 266 (1974).
162. V. Delaroff and R. Viennet, Bull. Soc. Chim. France, 277 (1972).
163. J. K. Gawronski, S. M. Reddy and H. M. Walborsky, J. Am. Chem. Soc, 109, 6726 (1987).