Static and Dynamic Stereochemistry of Push‐Pull and Strained Ethylenes

Static and Dynamic Stereochemistry of Push-Pull and Strained Ethylenes Jan Sandströum, Jan Sandströum Division of Organic Chemistry 3, Chemical Center, University of Lund, Lund, SwedenSearch for more papers by this author Jan Sandströum, Jan Sandströum Division of Organic Chemistry 3, Chemical Center, University of Lund, Lund, SwedenSearch for more papers by this author Book Editor(s):Norman L. Allinger, Norman L. Allinger University of Georgia, Athens, GeorgiaSearch for more papers by this authorErnest L. Eliel, Ernest L. Eliel University of North Carolina, Chapel Hill, North CarolinaSearch for more papers by this authorSamuel H. Wilen, Samuel H. Wilen City College, City University of New York, New York, New YorkSearch for more papers by this author First published: 01 January 1983 https://doi.org/10.1002/9780470147238.ch2Citations: 149Book Series:Topics in Stereochemistry AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary This chapter contains sections titled: Introduction Push-Pull Ethylenes Ground State and Transition State Properties Strained Ethylenes without Push-Pull Effect Ab Initio Calculations Conclusion References Douglas, J. E.; Rabinovitch, B. S.; Looney, F. S. J. Chem. Phys., 1955, 23, 315. Rabinovitch, B. S.; Michel, K.-W. J. Am. Chem. Soc., 1959, 81, 5056. Cundall, R. B.; Palmer, T. F. Trans. Faraday Soc., 1961, 57, 1936. Lin, M. C.; Laidler, K. J. Can. J. Chem., 1968, 46, 973. Hawton, L. D.; Semeluk, G. P. Can. J. Chem., 1966, 44, 2143. Butler, J. N.; McAlpine, R. D. Can. J. Chem., 1963, 41, 2487. Kistiakovsky, G. B.; Smith, W. R. J. Am. Chem. Soc., 1934, 56, 638. Kistiakovsky, G. B.; Smith, W. R. J. Am. Chem. Soc., 1936, 58, 2428. Kistiakovsky, G. B.; Smith, W. R. J. Am. Chem. Soc., 1935, 57, 269. Calvin, M.; Alter, H. W. J. Chem. Phys., 1951, 19, 768. Kost, D.; Carlson, E. H.; Raban, M. J. Chem. Soc., Chem. Commun., 1971, 656. Kalinowski, H.-O.; Kessler, H. Top. Stereochem., 1973, 7, 303. Jackman, L. M., In “ Dynamic Nuclear Magnetic Resonance”; L. M. Jackman; F. A. Cotton; Eds.; Academic Press: London and New York, 1975, p. 203. Dabrowski, J.; Kozerski, L. J. Chem. Soc., B, 1971, 345. Dabrowski, J.; Kozerski, L. Org. Magn. Reson., 1972, 4, 137. Kozerski, L.; Dabrowski, J. Org. Magn. Reson., 1972, 4, 253. Dabrowski, J.; Kamiénska-Trela, K. Org. Magn. Reson., 1972, 4, 421. Kozerski, L.; Dabrowski, J. Org. Magn. Reson., 1973, 5, 459. Dabrowski, J.; Kozerski, L. Org. Magn. Reson., 1973, 5, 469. Filleux-Blanchard, M.-L.; Clesse, F.; Bignebat, J.; Martin, G. J. Tetrahedron Lett., 1969, 981. Kleinpeter, E.; Pulst, M. Org. Magn. Reson., 1977, 9, 308. Filleux-Blanchard, M.-L.; Durand, H.; Martin, G. J. Org. Magn. Reson., 1970, 2, 539. Filleux-Blanchard, M.-L.; Mabon, F.; Martin, G. J. Tetrahedron Lett., 1974, 3907. Hobson, R. F.; Reeves, L. W. J. Phys. Chem., 1973, 77, 419. Kramer, H. E. A.; Gompper, R. Z. Phys. Chem., 1964, 43 (NF), 292. Piccinni-Leopardi, C.; Fabre, O.; Zimmerman, D.; Reisse, J.; Cornea, F.; Fulea, C. Can. J. Chem., 1977, 55, 2649. Czerwinska, E.; Kozerski, L.; Boksa, J. Org. Magn. Reson., 1976, 8, 345. Herbig, K.; Huisgen, R.; Huber, H. Chem. Ber., 1966, 99, 2546. Smith, D.; Taylor, P. J. Spectrochim. Acta, 1976, 32A, 1489 and earlier papers in the same series. Mannschreck, A.; Koelle, U. Tetrahedron Lett., 1967, 863. Shvo, Y.; Taylor, E. C.; Bartulin, J. Tetrahedron Lett., 1967, 3259. Shvo, Y.; Shanan-Atidi, H. J. Am. Chem. Soc., 1969, 91, 6683. Shvo, Y.; Shanan-Atidi, H. J. Am. Chem. Soc., 1969, 91, 6689. Dahlqvist, K.-I. Acta Chem. Scand., 1970, 24, 1941. Osman, R.; Shvo, Y. Tetrahedron, 1978, 34, 2321. Koelle, U.; Kolb, B.; Mannschreck, A. Chem. Ber., 1980, 113, 2545. Uray, G.; Wolfbeis, O. S.; Junek, H. J. Mol. Struct., 1979, 54, 77. Bakhmutov, V. I.; Burmistrov, V. A. Org. Magn. Reson., 1979, 12, 185. Fallon, G. D.; Gatehouse, B. M.; Pring, A.; Rae, I.; Weigold, J. A. Can. J. Chem., 1980, 58, 821. Senning, A.; Kelly, P. Acta Chem. Scand., 1972, 26, 2877. Shvo, Y. Tetrahedron Lett., 1968, 5923. Shvo, Y.; Belsky, I. Tetrahedron, 1969, 25, 4649. Kuo, Y.-N.; Chen, F.; Ainsworth, C. J. Chem. Soc. Chem. Commun., 1971, 137. Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem., 1972, 46, 59. Sandström, J.; Wennerbeck, I. Acta Chem. Scand., 1970, 24, 1191. Dreier, C.; Henriksen, L.; Karlsson, S.; Sandström, J. Acta Chem. Scand., 1978, B 32, 281. Isaksson, G.; Sandström, J. Acta Chem. Scand., 1973, 27, 1183. Le Botlan, D.; Filleux-Blanchard, M.-L.; le Coustumer, G.; Mollier, Y. Org. Magn. Reson., 1974, 6, 454. Berg, U.; Sandström, J. Acta Chem. Scand., 1978, B32, 41. Sandström, J.; Wennerbeck, I. Acta Chem. Scand., 1978, B32, 421. Wennerbeck, I.; Sandström, J. Org. Magn. Reson., 1972, 4, 783. Fernholt, L.; Samdal, S.; Seip, R. J. Mol. Struct., 1981, 72, 217. Sandström, J.; Sjöstrand, U.; Wennerbeck, I. J. Am. Chem. Soc., 1977, 99, 4526. Kessler, H. Chem. Ber., 1970, 103, 973. Eicher, T.; Pelz, N. Chem. Ber., 1970, 103, 2647. Eicher, T.; Weber, J. L. Top. Curr. Chem., 1975, 57, 1. Crabtree, J. H.; Bertelli, D. J. J. Am. Chem. Soc., 1967, 89, 5384. Downing, A. P.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc, 1969B, 111. Hartke, K.; Salamon, G. Chem. Ber., 1970, 103, 147. Olsson, T.; Sandström, J. Acta Chem. Scand., 1982, B36, 23. Bergmann, E. D.; Agranat, I. J. Chem. Soc. Chem. Commun., 1965, 512. Prinzbach, H.; Knöfel, H.; Woischnik, E., In “ Aromaticity, Pseudoaromaticity, Anti-aromaticity,” The Jerusalem Symposia on Quantum Chemistry and Biochemistry III; Bergmann, E. D.; Pullman, B., Eds.; Jerusalem, 1971, p. 269. Dewar, M. J. S.; Gleicher, G. J. J. Am. Chem. Soc., 1965, 87, 685. Kende, A. S.; Izzo, P. T.; Fulmor, W. Tetrahedron Lett., 1966, 3697. Mannschreck, A.; Kolb, B. Chem. Ber., 1972, 105, 696. Hafner, K. Angew. Chem., 1963, 75, 1041; Angew. Chem. Int. Ed. Engl., 1964, 3, 165. Bertelli, D. J.; Crews, P. O.; Griffin, S. Tetrahedron, 1968, 24, 1945. Prinzbach, H.; Knöfel, H. Angew. Chem., 1969, 81, 900; Angew. Chem. Int. Ed. Engl., 1969, 8, 821. Hafner, K.; Tappe, H. Angew. Chem., 1969, 81, 564; Angew. Chem. Int. Ed. Engl., 1969, 8, 593. Braun, S.; Hafner, K.; Lindner, H.-J., personal communication. Boche, G.; Heidenhain, F. Angew. Chem., 1978, 90, 290; Angew. Chem. Int. Ed. Engl., 1978, 17, 283. Rabiller, C.; Ricolleau, G.; Martin, M. L.; Martin, G. J. Nouveau J. Chim., 1980, 4, 35. Boche, G.; Heidenhain, F. J. Am. Chem. Soc., 1979, 101, 738. Boche, G.; Heidenhain, F.; Thiel, W.; Eiben, R. Chem. Ber. 1982, 115, 3167. Jackman, L. M.; Haddon, R. C. J. Am. Chem. Soc., 1973, 95, 3687. Brown, J. P.; Jackman, L. M., unpublished results, quoted in ref. 13, p. 241. Seitz, G. Angew. Chem., 1969, 81, 518; Angew. Chem. Int. Ed. Engl., 1969, 8, 478. Belsky, I.; Dodiuk, H.; Shvo, Y. J. Org. Chem., 1977, 42, 2734. Taft, R. W., Jr., In “ Steric Effects in Organic Chemistry”; M. S. Newman, Ed.; Wiley: New York, 1956, pp. 578, 599. Kretschmer, M.; Kleinpeter, E.; Pust, M.; Borsdorf, R., personal communication. Berg, U., Thesis, Lund, 1974. Radeglia, R. Z. Phys. Chem., 1967, 235, 335. Blanchard, M. L.; Chevallier, A.; Martin, G. J. Tetrahedron Lett., 1967, 5057. Dahlqvist, K.-I.; Forsén, S. Acta Chem. Scand., 1970, 24, 2075. Prokof'ev, E. P.; Krasnaya, Zh. A.; Kucherov, V. F. Org. Magn. Reson., 1974, 6, 240. Michalik, M.; Peseke, K.; Radeglia, R. J. prakt. Chem., 1981, 323, 506. Sandström, J.; Wennerbeck, I. J. Chem. Soc. Chem. Commun., 1971, 1088. Sandström, J.; Sjöstrand, U. Tetrahedron, 1978, 34, 371. Sjöstrand, U.; Sandström, J. Tetrahedron, 1978, 34, 3305. Allinger, N. L.; Sprague, J. T. J. Am. Chem. Soc., 1972, 94, 5734. Coulson, C. A. Proc. Roy. Soc., 1939, A169, 413. Bak, B.; Hansen-Nygaard, L. J. Chem. Phys., 1960, 33, 418. Bartell, L. S.; Roth, E. A.; Hollowell, C. D.; Kuclitsu, K. S.; Young, J. E. J. Chem. Phys., 1965, 42, 2683. Rihs, G.; Niederhauser, A.; Sterchi, A.; Neuenschwander, M. Chimia, 1976, 30, 52. Hazell, A.; Mukhopadhyay, A. Acta Cryst., 1980, B36, 747. Ammon, H. L. J. Am. Chem. Soc., 1973, 95, 7093. Ammon, H. L.; Sherrer, C.; Eicher, T. Acta Cryst., 1978, B34, 3782. Ammon, H. L.; Sherrer, C.; Agranat, I. Chem. Scripta, 1977, 11, 39. Burzlaff, H.; Hartke, K.; Salamon, R. Chem. Ber., 1970, 103, 156. Kennard, O.; Watson, D. G.; Fawcett, J. K.; Kerr, K. A. Tetrahedron Lett., 1967, 3885. Shimanouchi, H.; Sasada, Y.; Ashida, T.; Kakudo, H.; Murata, I.; Kitahara, Y. Acta Cryst., 1969, B25, 1890. Abrahamsson, S.; Rehnberg, G.; Liljefors, T.; Sandström, J. Acta Chem. Scand., 1974, B28, 1109. Shmueli, U.; Shanan-Atidi, H.; Horwitz, H.; Shvo, Y. J. Chem. Soc, Perkin, Trans. 2, 1973, 657. Burzlaff, H.; Kaweda, I. Chem. Ber., 1969, 102, 3632. Ammon, H. L.; Wheeler, G. L. J. Am. Chem. Soc., 1975, 97, 2326. Ammon, H. L. Acta Cryst., 1974, B30, 1731. Adhikesavalu, D.; Venkatesan, K., personal communication. Adhikesavalu, D.; Venkatesan, K. Acta Cryst., 1981, B37, 2048. Ammon, H. L. Acta Cryst., 1976, B32, 2693. Böhme, R.; Burzlaff, H. Chem. Ber., 1974, 107, 832. Shimanouchi, H.; Ashida, T.; Sasada, Y.; Kakudo, M.; Murata, I.; Kitahara, Y. Bull. Chem. Soc., Japan, 1966, 39, 2322. 111(b) Shimanouchi, H.; Sasada, Y.; Kabato, C.; Kitahara, Y. Acta Cryst., 1974, B30, 1267. Shimanouchi, H.; Sasada, Y.; Kabato, C.; Kitahara, Y. Acta Cryst., 1974, B30, 1273. Sandström, J.; Wennerbeck, I., unpublished results. Osman, R.; Zunger, A.; Shvo, Y. Tetrahedron, 1978, 34, 2315. Thomas, R.; Coppens, P. Acta Cryst., 1972, B28, 1800. Ericsson, E.; Marnung, T.; Sandström, J.; Wennerbeck, I. J. Mol. Struct., 1975, 24, 373. Bergmann, E. D.; Agranat, I. J. Am. Chem. Soc., 1964, 86, 3587. Andreades, S. J. Am. Chem. Soc., 1965, 87, 3941. Agranat, I.; Pick, M. R. Tetrahedron Lett., 1973, 4079. Hartke, K.; Schmidt, E.; Castillo, M.; Bartulin, J. Chem. Ber., 1966, 99, 3269. Hafner, K.; Schultz, G.; Wagner, K. Justus Liebigs Ann. Chem., 1964, 678, 39. Nakajima, T.; Kohda, S.; Tajiri, A.; Karasawa, S. Tetrahedron, 1967, 23, 2189. Kitahara, Y.; Murata, I.; Ueno, M.; Sato, K.; Watanabe, H. J. Chem. Soc. Chem. Commun., 1966, 180. Murata, I.; Ueno, M.; Kitahara, Y.; Watanabe, H. Tetrahedron Lett., 1966, 1831. Bergmann, E. D.; Agranat, I. Tetrahedron, 1966, 22, 1275. Gompper, R.; Schmidt, R. R.; Kutter, E. Justus Liebigs Ann. Chem., 1965, 684, 37. Föhlisch, B.; Bürgle, P. Justus Liebigs Ann. Chem., 1967, 701, 67. Yamakama, M.; Watanabe, H.; Mukai, T.; Nozoe, T.; Kubo, M. J. Am. Chem. Soc., 1960, 82, 5665. Koopmans, T. A. Physica, 1933, 1, 104. Betteridge, D.; Henriksen, L.; Sandström, J.; Wennerbeck, I.; Williams, M. A. Acta Chem. Scand., 1977, A31, 14. Colonna, F. P.; Distefano, G.; Sandström, J.; Sjöstrand, U. J. Chem. Soc., Perkin Trans. 2, 1978, 279. Bernardi, F.; Mangini, A.; Epiotis, N. D.; Larson, J. R.; Shaik, S. J. Am. Chem. Soc., 1977, 99, 7465. Ramsey, B. G.; Taft, R. W. J. Am. Chem. Soc., 1966, 88, 3058. Olofson, R. A.; Walinsky, S. W.; Marino, J. P.; Jernow, J. L. J. Am. Chem. Soc., 1968, 90, 6554. Henriksen, L.; Sandström, J., unpublished results. Exner, O., In “ Advances in Linear Free Energy Relationships”; N. B. Chapman; J. Shorter, Eds.; Plenum Press: London and New York, 1972, p. 37. Bordwell, F. G.; Matthews, W. S. J. Am. Chem. Soc., 1974, 96, 1216. Epiotis, N. D.; Cherry, W. R.; Shaik, S.; Yates, R. L.; Bernardi, F. Top. Curr. Chem., 1977, 70, 9. Sandström, J. Tetrahedron Lett., 1979, 639. Kalinowski, H.-O.; Kessler, H.; Walter, A. Tetrahedron, 1974, 30, 1137. Reichardt, C.; Dimroth, K. Top. Curr. Chem., 1968, 11, 1. Böttcher, C. J. F. “ Theory of Electric Polarization”; Elsevier: Amsterdam, 1952; Chapter 3. Berg, U.; Sjöstrand, U. Org. Magn. Reson., 1978, 11, 555. Anet, F. A. L.; Anet, R., Ref. 13, p. 575. Rieker, A.; Kessler, H. Chem. Ber., 1969, 102, 2147. Hitchcock, P. B. J. Chem. Soc. Dalton Trans., 1979, 1317. Ammon, H. L.; Wheeler, G. L.; Agranat, I. Tetrahedron, 1973, 29, 2695. Fallon, L.; Ammon, H. L.; West, R.; Rao, V. N. M. Acta Cryst., 1974, B30, 2407. Bailey, N. P.; Hull, S. E. Acta Cryst., 1978, B34, 3289. Mills, J. F. D.; Nyburg, S. C. J. Chem. Soc., 1963, 308. Harnik, E.; Schmidt, G. M. J. J. Chem. Soc., 1954, 3295. Gault, I. R.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc. Chem. Commun., 1970, 269. Nyburg, C. S. Acta Cryst., 1954, 7, 779. Agranat, I.; Rabinowitz, M.; Weitzen-Dagan, A.; Gosnay, I. J. Chem. Soc. Chem. Commun., 1972, 732. Hirsch, J. Top. Stereochem., 1967, 1, 199. Lenoir, D.; Lemmen, P. Chem. Ber., 1980, 113, 3112. Allinger, N. L.; Sprague, J. T. J. Am. Chem. Soc., 1973, 95, 3893. Allinger, N. L.; Liljefors, T. J. Am. Chem. Soc., 1974, 96, 5100. Rabinovitz, M.; Agranat, I.; Weitzen-Dagan, A. Tetrahedron Lett., 1974, 1241. Agranat, I.; Rabinovitz, M.; Gosnay, I.; Weitzan-Dagan, A. J. Am. Chem. Soc., 1972, 94, 2889. Agranat, I.; Tapuhi, Y. J. Am. Chem. Soc., 1976, 98, 615. Agranat, I.; Tapuhi, Y. Nouveau J. Chim., 1977, 1, 361. Agranat, I.; Tapuhi, Y. J. Am. Chem. Soc., 1978, 100, 5604. Agranat, I.; Tapuhi, Y. J. Am. Chem. Soc., 1979, 101, 665. Agranat, I.; Tapuhi, Y.; Lallemand, J. Y. Nouveau J. Chim., 1979, 3, 59. Agranat, I.; Tapuhi, Y. J. Org. Chem., 1979, 44, 1941. Tapuhi, Y.; Kalisky, O.; Agranat, I. J. Org. Chem., 1979, 44, 1949. Korenstein, R.; Muszkat, K. A.; Sharafy-Ozeri, S. J. Am. Chem. Soc., 1973, 95, 6177. Korenstein, R.; Muszkat, K. A.; Slifkin, M. A.; Fischer, E. J. Chem. Soc., Perkin Trans. 2, 1976, 438. Rauk, A.; Jarvie, J. O.; Ichimura, H.; Barriel, J. M. J. Am. Chem. Soc., 1975, 97, 5656. Scott, A. I.; Wrixon, A. D. J. Chem. Soc. Chem. Commun., 1970, 43. See Charney, E. “ The Molecular Basis of Optical Activity”; Wiley: New York, 1979; pp. 202 ff for a discussion and review of this problem. Yaris, M.; Moscowitz, A.; Berry, R. S. J. Chem. Phys., 1968, 49, 3150. Gavin, R. M.; Wang, Z. F. J. Am. Chem. Soc., 1973, 95, 1425. Traetteberg, M. Acta Chem. Scand., 1975, B29, 29. Ermer, O.; Lifson, S. J. Am. Chem. Soc., 1973, 95, 4121. Traetteberg, M.; Bakken, P.; Almenningen, A. J. Mol. Struct., 1981, 74, 321. Allinger, N. L. J. Am. Chem. Soc., 1977, 99, 8127. Ermer, O. Struct. Bonding (Berlin), 1976, 27, 161. Inoue, Y.; Veoka, T.; Kuroda, T.; Hakushi, T. J. Chem. Soc. Chem. Commun., 1981, 1031. Bonneau, R.; Forner de Violet, P.; Joussot-Dubien, J. Nouveau J. Chim., 1977, 1, 31. Bonneau, R.; Joussot-Dubien, J.; Yarwood, J.; Pereyre, J. Tetrahedron Lett., 1977, 235. Bonneau, R.; Joussot-Dubien, J.; Salem, L.; Yarwood, A. J. J. Am. Chem. Soc., 1976, 98, 4329. McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem., 1978, 42, 3255. Back, T. G.; Barton, D. H. R.; Britten-Kelly, M. R.; Guziec, F. S., Jr. J. Chem. Soc., Perkin Trans. 1, 1976, 2079. Ermer, O.; Lifson, S. Tetrahedron, 1974, 30, 2425. Lenoir, D.; Dauner, H.; Frank, R. M. Chem. Ber., 1980, 113, 2636. Burkert, U. Tetrahedron, 1981, 37, 333. Favini, G.; Simonetta, M.; Todeschini, R. J. Comput. Chem., 1981, 2, 149. Andose, J.; Engler, E.; Collins, J. B.; Hummel, J. P.; Mislow, K.; von R. Schleyer, P. QCPE 1978, 11, 348. Mugnoli, A.; Simonetta, M. J. Chem. Soc., Perkin Trans. 2, 1976, 1831. Swen-Walstra, S. C.; Visser, G. J. J. Chem. Soc. Chem. Commun., 1971, 82. Lenoir, D.; Frank, R. M.; Cordt, F.; Gieren, A.; Lamm, V. Chem. Ber., 1980, 113, 739. Pilati, T.; Simonetta, M. J. Chem. Soc., Perkin Trans. 2, 1977, 1435. Feringa, B.; Wynberg, H. J. Am. Chem. Soc., 1977, 99, 602. Neuman, M. S.; Lednicer, D. J. Am. Chem. Soc., 1965, 87, 4765. Sakurai, H.; Nakadaira, Y.; Kira, M.; Tobita, H. Tetrahedron Lett., 1980, 21, 3077. Sakurai, H.; Tobita, H.; Kira, M.; Nakadaira, Y. Angew. Chem., 1980, 92, 632; Angew. Chem. Int. Ed. Engl., 1980, 19, 620. Sakurai, H.; Nakadaira, Y.; Tobita, H.; Ito, T.; Toriumi, K.; Ito, H. J. Am. Chem. Soc., 1982, 104, 300. Apeloig, Y.; von Schleyer, R. P.; Binkley, J. S.; Pople, J. A. J. Am. Chem. Soc., 1976, 98, 4332. Laidig, W. D.; Schaefer, H. F., III. J. Am. Chem. Soc., 1979, 101, 7184. Morrison, J. A., Chung, C.; Lagow, R. J. J. Am. Chem. Soc., 1975, 97, 5015. Krogh-Jesperson, K.; Cremer, D.; Poppinger, D.; Pople, J. A.; von Schleyer, R. P.; Chandrasekhar, J. J. Am. Chem. Soc., 1979, 101, 4843. Apeloig, Y.; Clark, T.; Kos, A. J.; Jemmis, E. D.; von Schleyer, R. P. Isr. J. Chem., 1980, 20, 43. Bonacic-Koutecky, V.; Bruckman, P.; Hiberty, P.; Koutecky, J.; Leforestier, C.; Salem, L. Angew. Chem., 1975, 87, 599; Angew. Chem. Int. Ed. Engl., 1975, 14, 575. Brooks, B. R.; Schaefer, H. F., III. J. Am. Chem. Soc., 1979, 101, 307. Salem, L. Acc. Chem. Res., 1979, 12, 87. Boche, G.; Eiben, R.; Thiel, W. Angew. Chem., 1982, 94, 703. Angew. Chem. Suppl., 1982, 1535. Angew. Chem. Int. Ed. Engl. 1982, 21, 688. Berg, U.; Isaksson, R.; Sandström, J.; Sjöstrand, U.; Eiglsperger, A.; Mannschreck, A. Tetrahedron Lett. 1982, 23, 4237. Olsen, B. A.; and Evans, D. H. J. Am. Chem. Soc., 1981, 103, 839. Hammerich, O.; Parker, V. D. Acta Chem. Scand. 1981, B35, 395. Badar, Y.; Cooke, A. S.; Harris, M. M. J. Chem. Soc., C. 1966, 1315. Ahlberg, E.; Hammerich, O.; Parker, V. D. J. Am. Chem. Soc., 1981, 103, 844. Neta, P.; Evans, D. H. J. Am. Chem. Soc., 1981, 103, 7041. Leigh, W. J.; Arnold, D. R. Can. J. Chem. 1981, 59, 609. Baldock, R. W.; Hudson, P.; Katritzky, A. R.; Soti, F. J. Chem. Soc., Perkin Trans. 1 1974, 1422. Viehe, H. G.; Merenyi, R.; Stella, L.; Janousek, Z. Angew. Chem. 1979, 91, 982. Angew. Chem. Int. Ed. Engl. 1979, 18, 917. Sakurai, H.; Tobita, H.; Nakadaira, Y.; Kabuto, C. J. Am. Chem. Soc., 1982, 104, 4288. Hseu, T.-H.; Chi, Y.; Liu, C.-S. J. Am. Chem. Soc., 1982, 104, 1594. Maier, W. F.; von Schleyer, R. P. J. Am. Chem. Soc., 1981, 103, 1981. Wiesman, J. R.; Pletcher, W. A. J. Am. Chem. Soc., 1970, 92, 956. Kamath, N.; Venkatesan, K., Private communication. Citing Literature Topics in Stereochemistry, Volume 14 ReferencesRelatedInformation