메뉴 건너뛰기




Volumn 99, Issue 5, 1999, Pages 1387-1413

Face Selection in Addition and Elimination in Sterically Unbiased Systems

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0000152317     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr980364y     Document Type: Article
Times cited : (66)

References (296)
  • 26
    • 33947332027 scopus 로고
    • For a fuller discussion of stereochemical descriptors, see: (a) Hanson, K. R. J. Am. Chem. Soc. 1966, 88, 2731.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2731
    • Hanson, K.R.1
  • 39
    • 84986769154 scopus 로고
    • (a) Srivastava, S.; Cheung, C. K.; le Noble, W. J. Magn. Res. Chem. 1985, 23, 232; 1989, 27, II.
    • (1989) Magn. Res. Chem. , vol.27
  • 42
    • 37049137978 scopus 로고
    • Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447 and earlier papers quoted therein. For an entirely different approach toward the confirmation of retentive solvolysis of 2-adamantyl esters, see Nordlander, J. E.; Kotian, K. D.; Raff, D. E.; Grohol, W. P.; Vishwanuth, V. M.; Winemiller, J. J. J. Am. Chem. Soc. 1988, 105, 863.
    • (1975) J. Chem. Soc., Perkin Trans. 2 , vol.1447
    • Bone, J.A.1    Pritt, J.R.2    Whiting, M.C.3
  • 43
    • 33845552678 scopus 로고
    • Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447 and earlier papers quoted therein. For an entirely different approach toward the confirmation of retentive solvolysis of 2-adamantyl esters, see Nordlander, J. E.; Kotian, K. D.; Raff, D. E.; Grohol, W. P.; Vishwanuth, V. M.; Winemiller, J. J. J. Am. Chem. Soc. 1988, 105, 863.
    • (1988) J. Am. Chem. Soc. , vol.105 , pp. 863
    • Nordlander, J.E.1    Kotian, K.D.2    Raff, D.E.3    Grohol, W.P.4    Vishwanuth, V.M.5    Winemiller, J.J.6
  • 46
    • 0001071294 scopus 로고
    • Cheung, C. K; Tseng, L. T.; Lin, M.-h.; Srivastava, S.; le Noble, W. J. J. Am. Chem. Soc. 1986, 108, 1598; 1987, 109, 7239.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7239
  • 53
    • 84988101428 scopus 로고
    • see also ref 44 and 198 below
    • Herrmann, R.; Kirmse, W. Liebigs Ann. Chem. 1995, 699 (see also ref 44 and 198 below).
    • (1995) Ann. Chem. , pp. 699
    • Herrmann, R.1    Liebigs, K.W.2
  • 58
    • 0000880626 scopus 로고
    • Laube, T. Acc. Chem. Res. 1995, 28, 399. Laube comments: ''bridging and hyperconjugation are related phenomena, but hyperconjugation does not lead to such strong changes of geometry as observed for bridging. There is no clear boundary between these two effects; they are considered as regions in the spectrum of charge delocalization effects between the extreme cases "no charge delocalization" and "strong charge delocalization with bridging." To the present authors, this description is a perfect example of the arbitrariness in drawing distinctions between bridging, hyperconjugation, sigma delocalization, neighboring group effects, etc.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 399
    • Laube, T.1
  • 59
    • 84987378192 scopus 로고
    • Laube, T.; Hollenstein, S. Helv. Chim. Acta 1994, 77, 1773. The structure of the 1,3,7-trimethyladamant-5-yl cation was also reported to show such effects: Laube, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 349.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 1773
    • Laube, T.1    Hollenstein, S.2
  • 60
    • 84985597804 scopus 로고
    • Laube, T.; Hollenstein, S. Helv. Chim. Acta 1994, 77, 1773. The structure of the 1,3,7-trimethyladamant-5-yl cation was also reported to show such effects: Laube, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 349.
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 349
    • Laube, T.1
  • 62
    • 0001035426 scopus 로고
    • See also Laube, T.; Ha, T.-K. J. Am. Chem. Soc. 1988, 110, 5511. Laube, T. J. Am. Chem. Soc. 1993, 115, 7240. Yannoni, C. S.; Kendrick, R. D.; Myhre, P. C.; Bebout, D. C.; Petersen, B. L. J. Am. Chem. Soc. 1989, 111, 6440.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5511
    • Laube, T.1    Ha, T.-K.2
  • 63
    • 0347307522 scopus 로고
    • See also Laube, T.; Ha, T.-K. J. Am. Chem. Soc. 1988, 110, 5511. Laube, T. J. Am. Chem. Soc. 1993, 115, 7240. Yannoni, C. S.; Kendrick, R. D.; Myhre, P. C.; Bebout, D. C.; Petersen, B. L. J. Am. Chem. Soc. 1989, 111, 6440.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7240
    • Laube, T.1
  • 66
    • 0000130172 scopus 로고
    • Adcock, W.; Iyer, V. S. J. Org. Chem. 1988, 53, 5259. Adcock, W.; Iyer, V. S. Magn. Res. Chem. 1991, 29, 381.
    • (1988) J. Org. Chem. , vol.53 , pp. 5259
    • Adcock, W.1    Iyer, V.S.2
  • 67
    • 84989064941 scopus 로고
    • Adcock, W.; Iyer, V. S. J. Org. Chem. 1988, 53, 5259. Adcock, W.; Iyer, V. S. Magn. Res. Chem. 1991, 29, 381.
    • (1991) Magn. Res. Chem. , vol.29 , pp. 381
    • Adcock, W.1    Iyer, V.S.2
  • 69
    • 0001374492 scopus 로고
    • Adcock, W.; Trout, N. A. J. Org. Chem. 1991, 56, 3229. Adcock, W.; Trout, N. A. Magn. Res. Chem. 1998, 36, 181.
    • (1991) J. Org. Chem. , vol.56 , pp. 3229
    • Adcock, W.1    Trout, N.A.2
  • 70
  • 77
    • 0347937715 scopus 로고
    • The 4-oxo-substituted 2-adamantyl esters furnish an example. See: Yoshida, M.; Kurihara, Y.; Takeuchi, K. Synth. Commun. 1992, 20, 3529 and Yoshida, M.; Mitsyhashi, K.; Kimura, T.; Takeuchi, K.; Fukuyo, E.; Yanagi, K. Chem. Lett. 1992, 1771.
    • (1992) Synth. Commun. , vol.20 , pp. 3529
    • Yoshida, M.1    Kurihara, Y.2    Takeuchi, K.3
  • 81
    • 0001548626 scopus 로고
    • Hirsl-Starcevic, S.; Majerski, Z. J. Org. Chem. 1982, 47, 2520. Note that this carbene has a singlet groundstate: Bally, T.; Matsinger, S.; Truttmann, L.; Platz, M. S.; Morgan, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1964.
    • (1982) J. Org. Chem. , vol.47 , pp. 2520
    • Hirsl-Starcevic, S.1    Majerski, Z.2
  • 92
    • 37049107831 scopus 로고
    • We take parenthetic note here of the many modifiers that have been introduced for the concept of hyperconjugation: positive, neutral, negative (which includes but is not limited to the anomeric effects (both exo and endo), reverse and anionic, not to mention no-bond resonance, and the myriad of terms introduced during the "carbonium ion controversy". Although the energetics of the various manifestations of electron delocalization can differ greatly from case to case, we feel that it is not always profitable to draw so many distinctions. However, we do use the terms Anh-, Felkin-, and Cieplak models here (even though all three revolve about hyperconjugative interactions) because the first two of these assume distortions in the transition state which are critical to their success in accounting for cyclohexanone stereochemistry. See (a) Booth, H.; Khedhair, K. A. J. Chem. Soc., Chem. Commun. 1985, 467.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 467
    • Booth, H.1    Khedhair, K.A.2
  • 120
    • 1542738935 scopus 로고
    • Hahn, J. M.; le Noble. W. J. J. Am. Chem. Soc. 1992, 114, 1916. For a computational study of this system, see Coxon, J, M.; Houk, K N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1916
    • Hahn, J.M.1    Le Noble, W.J.2
  • 121
    • 33751154573 scopus 로고
    • Hahn, J. M.; le Noble. W. J. J. Am. Chem. Soc. 1992, 114, 1916. For a computational study of this system, see Coxon, J, M.; Houk, K N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418.
    • (1995) J. Org. Chem. , vol.60 , pp. 418
    • Coxon, J.M.1    Houk, K.N.2    Luibrand, R.T.3
  • 137
    • 0000655128 scopus 로고
    • Bodepudi, V. R.; le Noble, W. J. J. Org. Chem. 1994, 59, 3265. For references to the protonation stereochemistry of cyclohex- anone enolates, see Zimmerman, H. E. Acc. Chem. Res. 1987, 20, 263.
    • (1994) J. Org. Chem. , vol.59 , pp. 3265
    • Bodepudi, V.R.1    Le Noble, W.J.2
  • 138
    • 0001302486 scopus 로고
    • Bodepudi, V. R.; le Noble, W. J. J. Org. Chem. 1994, 59, 3265. For references to the protonation stereochemistry of cyclohex-anone enolates, see Zimmerman, H. E. Acc. Chem. Res. 1987, 20, 263.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 263
    • Zimmerman, H.E.1
  • 147
    • 0000051812 scopus 로고
    • Halterman, R. L.; McEvoy, M. A. J. Am. Chem. Soc. 1990, 112, 6690. Similar studies employing neighboring oxygen and sulfur atoms rather than p-substituted phenyl rings were recently reported: Dimitroff, M.; Fallis, A. G. Tetrahedron Lett. 1998, 39, 2527 and 2531.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6690
    • Halterman, R.L.1    McEvoy, M.A.2
  • 148
    • 0032559992 scopus 로고    scopus 로고
    • Halterman, R. L.; McEvoy, M. A. J. Am. Chem. Soc. 1990, 112, 6690. Similar studies employing neighboring oxygen and sulfur atoms rather than p-substituted phenyl rings were recently reported: Dimitroff, M.; Fallis, A. G. Tetrahedron Lett. 1998, 39, 2527 and 2531.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2527
    • Dimitroff, M.1    Fallis, A.G.2
  • 175
    • 0040478833 scopus 로고
    • Mohamadi has reported that the epoxidation of 3-cyclopentenyl-and 3-cyclohexenyl-N-i-propylacetamide with MCPBA gives the contrasteric syn product in a 20:1 ratio; see Mohamadi, F.; Spees, M. M. Tetrahedron Lett. 1988, 30, 1309.
    • (1988) Tetrahedron Lett. , vol.30 , pp. 1309
    • Mohamadi, F.1    Spees, M.M.2
  • 181
    • 0030739091 scopus 로고    scopus 로고
    • Gonikberg, E. M.; Picart, F.; le Noble, W. J. J. Org. Chem. 1996, 61, 9588; 1997, 62, 4885.
    • (1997) J. Org. Chem. , vol.62 , pp. 4885
  • 193
    • 25344452040 scopus 로고
    • Ph.D. Thesis, University of Groningen
    • Hummelen, J. C. Ph.D. Thesis, University of Groningen, 1985, 76 ff.
    • (1985)
    • Hummelen, J.C.1
  • 201
    • 0001736688 scopus 로고
    • See also Houk, K. N.; Mueller, P. H.; Wu, Y.-D.; Mazzochi, P. H.; Shook, D.; Khachik, F. Tetrahedron Lett. 1990, 31, 7285 and Burry, L. C.; Bridson, J. L.; Burnell, D. J. J. Org. Chem. 1995, 60, 5931.
    • (1995) J. Org. Chem. , vol.60 , pp. 5931
    • Burry, L.C.1    Bridson, J.L.2    Burnell, D.J.3
  • 241
    • 0024820755 scopus 로고
    • Lin, M.-h.; Boyd, M. K.; le Noble, W. J. J. Am. Chem. Soc. 1989, 111, 8746. As pointed out by a referee, this change in stereo-chemistry is analogous to the switch from anti to syn attack by nucleophiles in SN2 and SN2′ displacements; see March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 329 and literature quoted therein. The epimers 155 were formed as a 50/50 mixture in the reaction of methyllithium with the precusor ketone: no face selectivity was seen in that reaction.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8746
    • Lin, M.-H.1    Boyd, M.K.2    Le Noble, W.J.3
  • 242
    • 0024820755 scopus 로고
    • Wiley: New York
    • Lin, M.-h.; Boyd, M. K.; le Noble, W. J. J. Am. Chem. Soc. 1989, 111, 8746. As pointed out by a referee, this change in stereo- chemistry is analogous to the switch from anti to syn attack by nucleophiles in SN2 and SN2′ displacements; see March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 329 and literature quoted therein. The epimers 155 were formed as a 50/50 mixture in the reaction of methyllithium with the precusor ketone: no face selectivity was seen in that reaction.
    • (1992) Advanced Organic Chemistry, 4th Ed. , pp. 329
    • March, J.1
  • 253
    • 0346046208 scopus 로고
    • Their near-spherical shape renders adamantanones difficult targets for X-ray diffraction studies. However, 5-p-nitrophenyladamantan-2-one has been shown by this means to have a planar carbonyl group; the carbonyl bridge leans slightly (by 1.5°) in the direction of C-5. See Tafeenko, V. A.; Prozorovskii, A. E.; Kovalev, V. V.; Knyazeva, I. V. J. Struct. Chem. Engl. Transi. 1987, 28, 155. Planar carbonyl carbon is also observed in compound 44 (ref 84b) and in the tetracyclic 4,9-bridged adamantanone; see Inayama, S.; Singh, A. K.; Kawamata, T.; Iitaka, Y. Tetrahedron Lett. 1979, 1125.
    • (1987) J. Struct. Chem. Engl. Transi. , vol.28 , pp. 155
    • Tafeenko, V.A.1    Prozorovskii, A.E.2    Kovalev, V.V.3    Knyazeva, I.V.4
  • 254
    • 0018393067 scopus 로고
    • Their near-spherical shape renders adamantanones difficult targets for X-ray diffraction studies. However, 5-p-nitrophenyladamantan-2-one has been shown by this means to have a planar carbonyl group; the carbonyl bridge leans slightly (by 1.5°) in the direction of C-5. See Tafeenko, V. A.; Prozorovskii, A. E.; Kovalev, V. V.; Knyazeva, I. V. J. Struct. Chem. Engl. Transi. 1987, 28, 155. Planar carbonyl carbon is also observed in compound 44 (ref 84b) and in the tetracyclic 4,9-bridged adamantanone; see Inayama, S.; Singh, A. K.; Kawamata, T.; Iitaka, Y. Tetrahedron Lett. 1979, 1125.
    • (1979) Tetrahedron Lett. , pp. 1125
    • Inayama, S.1    Singh, A.K.2    Kawamata, T.3    Iitaka, Y.4
  • 275
    • 0346676899 scopus 로고    scopus 로고
    • Reference 115
    • (f) Reference 115.
  • 280
    • 0347937644 scopus 로고    scopus 로고
    • See also ref 9
    • (k) See also ref 9.
  • 283
    • 0025350075 scopus 로고
    • Haberfield, P.; Cincotta, J. J. J. Org. Chem. 1987, 52, 4627; 1990, 55, 1334.
    • (1990) J. Org. Chem. , vol.55 , pp. 1334
  • 286
    • 0346676901 scopus 로고    scopus 로고
    • See also ref 188j
    • See also ref 188j.
  • 290
    • 84963285908 scopus 로고
    • See also Durkin, K. A.; Liotta, D. J. Am. Chem. Soc. 1990, 112, 8162 and Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Williard, P. G, J. Am. Chem. Soc. 1998, 120, 7429.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8162
    • Durkin, K.A.1    Liotta, D.2
  • 294
    • 0001655451 scopus 로고
    • A referee has urged readers interested in the topic of hyperconjugation to read also the following classic papers on the subject: (a) Mulliken, R. S. Tetrahedron 1969, 5, 253.
    • (1969) Tetrahedron , vol.5 , pp. 253
    • Mulliken, R.S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.