SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 952-958

Experiments on the Chaperon effect in the nitration of aromatics

(4) Strazzolini, Paolo a Giumanini, Angelo G a Runcio, Antonio a Scuccato, Massimo a

a UNIVERSITY OF UDINE (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLBENZENE; AROMATIC AMIDE; PHENYLACETIC ACID;

ARTICLE; CHEMICAL STRUCTURE; DRUG CONFORMATION; ISOMER; NITRATION; OXIDATION; PROTON TRANSPORT; STEREOSPECIFICITY;

EID: 0032549043 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo9709763 Document Type: Article

Times cited : (35)

References (73)

1
- 84920292920
- note
- Students, enrolled in the Food Science doctoral degree curriculum at this institution, who were engaged in an organic chemistry full immersion summer stage (1996).

2
- 0039712603
- (a) Davis, G.; Cook, N. CHEMTECH 1977, 7, 626.
- (1977) Chemtech , vol.7 , pp. 626
- Davis, G.¹ Cook, N.²

3
- 0010661899
- (b) Bakke, J. M.; Hegbom, I. Acta Chem. Scand. 1994, 48, 181.
- (1994) Acta Chem. Scand. , vol.48 , pp. 181
- Bakke, J.M.¹ Hegbom, I.²

4
- 0010746353
- (c) Bakke, J. M.; Hegbom, I.; Øvreeide, E.; Aaby, K. Acta Chem. Scand. 1994, 48, 1001.
- (1994) Acta Chem. Scand. , vol.48 , pp. 1001
- Bakke, J.M.¹ Hegbom, I.² Øvreeide, E.³ Aaby, K.⁴

5
- 0000400756
- (d) Strazzolini, P.; Verardo, G.; Gorassini, F.; Giumanini, A. G. Bull. Chem. Soc. Jpn. 1995, 68, 1155.
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 1155
- Strazzolini, P.¹ Verardo, G.² Gorassini, F.³ Giumanini, A.G.⁴

6
- 0001755150
- (a) Gigante, B.; Prazeres, A. O.; Marcelo-Curto, M. J.; Cornélis, A.; Laszlo, P. J. Org. Chem. 1995, 60, 3445.
- (1995) J. Org. Chem. , vol.60 , pp. 3445
- Gigante, B.¹ Prazeres, A.O.² Marcelo-Curto, M.J.³ Cornélis, A.⁴ Laszlo, P.⁵

7
- 0001338710
- (b) Delaude, L.; Laszlo, P.; Smith, K. Acc. Chem. Res. 1993, 26, 607.
- (1993) Acc. Chem. Res. , vol.26 , pp. 607
- Delaude, L.¹ Laszlo, P.² Smith, K.³

8
- 0030031144
- (c) Riego, J. M.; Sedin, Z.; Zaldìvar, J. M.; Marziano, N. C.; Tortato, C. Tetrahedron Lett. 1996, 37, 513.
- (1996) Tetrahedron Lett , vol.37 , pp. 513
- Riego, J.M.¹ Sedin, Z.² Zaldìvar, J.M.³ Marziano, N.C.⁴ Tortato, C.⁵

9
- 37049090474
- (d) Suzuki, H.; Murashima, T. J. Chem. Soc., Perkin Trans. 1 1994, 903.
- (1994) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 903
- Suzuki, H.¹ Murashima, T.²

10
- 0001317422
- (e) Mori, T.; Suzuki, H. Synlett 1995, 383.
- (1995) Synlett , pp. 383
- Mori, T.¹ Suzuki, H.²

11
- 54249113412
- (f) Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans. 2 1996, 677.
- (1996) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 677
- Suzuki, H.¹ Mori, T.²

12
- 37049080491
- (a) Suzuki, H.; Tatsumi, A.; Ishibashi, T.; Mori, T. J. Chem. Soc., Perkin Trans. 1 1995, 339.
- (1995) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 339
- Suzuki, H.¹ Tatsumi, A.² Ishibashi, T.³ Mori, T.⁴

13
- 0001430331
- (b) Suzuki, H.; Takeuchi, T.; Mori, T. J. Org. Chem. 1996, 61, 5944.
- (1996) J. Org. Chem. , vol.61 , pp. 5944
- Suzuki, H.¹ Takeuchi, T.² Mori, T.³

14
- 0000113005
- Eberson, L.; Hartshorn, M. P.; Radner, F. Acta Chem. Scand. 1994, 48, 937.
- (1994) Acta Chem. Scand. , vol.48 , pp. 937
- Eberson, L.¹ Hartshorn, M.P.² Radner, F.³

15
- 0023829524
- R. C. Gaudreault et al. J. Pharm. Sci. 1988, 77, 185, reported a 50% separated yield of 2-nitrobenzenebutanoic acid (9a) and a 22% separated yield of 4-nitrobenzenebutanoic acid (9c). There is an obvious erroneous assignment of the location of the nitro groups caused by their inversion, as also evidenced by the comparison with the melting points reported in the literature (see Experimental Section).
- (1988) J. Pharm. Sci. , vol.77 , pp. 185
- Gaudreault, R.C.¹

16
- 84943982167
- Baas, J. M. A.; Wepster, B. M. Recl Trav. Chim. Pays-Bas 1971, 90, 1081.
- (1971) Recl Trav. Chim. Pays-Bas , vol.90 , pp. 1081
- Baas, J.M.A.¹ Wepster, B.M.²

17
- 84953878153
- Baas, J. M. A.; Wepster, B. M. Recl. Trav. Chim. Pays-Bas 1971, 90, 1089.
- (1971) Recl. Trav. Chim. Pays-Bas , vol.90 , pp. 1089
- Baas, J.M.A.¹ Wepster, B.M.²

18
- 84980116777
- (a) List, O. Chem. Ber. 1893, 26, 2451.
- (1893) Chem. Ber. , vol.26 , pp. 2451
- List, O.¹

19
- 85173720889
- (b) Neber, P. W.; Hartung, K.; Ruopp, W. Chem. Ber. 1925, 58, 1234.
- (1925) Chem. Ber. , vol.58 , pp. 1234
- Neber, P.W.¹ Hartung, K.² Ruopp, W.³

20
- 37049170139
- (c) Womack, E. B.; Campbell, N.; Dodds, G. B. J. Chem. Soc. 1938, 1402.
- (1938) J. Chem. Soc. , pp. 1402
- Womack, E.B.¹ Campbell, N.² Dodds, G.B.³

21
- 7144228846
- (d) Sugii, M.; Nakai, R. J. Org. Chem. 1957, 22, 288.
- (1957) J. Org. Chem. , vol.22 , pp. 288
- Sugii, M.¹ Nakai, R.²

22
- 37049057720
- Norman, R. O. C.; Radda, G. K. J. Chem. Soc. 1961, 3030.
- (1961) J. Chem. Soc. , pp. 3030
- Norman, R.O.C.¹ Radda, G.K.²

23
- 37049063302
- 2) strictly comparable to ours.
- (1961) J. Chem. Soc. , pp. 2938
- Knowles, J.R.¹ Norman, R.O.C.²

24
- 37049114273
- 2) strictly comparable to ours.
- (1971) J. Chem. Soc. B , pp. 2454
- Hartshorn, S.R.¹ Moodie, R.B.² Schofield, K.³

25
- 0001250936
- Ogata, Y.; Sawaki, Y. J. Am. Chem. Soc. 1966, 88, 5832.
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 5832
- Ogata, Y.¹ Sawaki, Y.²

26
- 0345301999
- Sparks, A. K. J. Org. Chem. 1966, 31, 2299.
- (1966) J. Org. Chem. , vol.31 , pp. 2299
- Sparks, A.K.¹

27
- 37049173454
- (a) Griffiths, P. H.; Walkey, W. A.; Watson, H. B. J. Chem. Soc. 1934, 631.
- (1934) J. Chem. Soc. , pp. 631
- Griffiths, P.H.¹ Walkey, W.A.² Watson, H.B.³

28
- 37049166492
- (b) Bunton, C. A.; Minkoff, G. J.; Reed, G. J. J. Chem. Soc. 1947, 1416.
- (1947) J. Chem. Soc. , pp. 1416
- Bunton, C.A.¹ Minkoff, G.J.² Reed, G.J.³

29
- 0006941589
- (c) Hoggett, J. G.; Moodie, R. B.; Schofield, K. J. Chem. Soc., Chem. Commun. 1969, 605.
- (1969) J. Chem. Soc., Chem. Commun. , pp. 605
- Hoggett, J.G.¹ Moodie, R.B.² Schofield, K.³

30
- 37049100438
- (d) Barnett, J. W.; Moodie, R. B.; Schofield, K.; Weston, J. B.; Coombes, R. G.; Golding, J. G.; Tobin, G. D. J. Chem. Soc., Perkin Trans. 2 1977, 248.
- (1977) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 248
- Barnett, J.W.¹ Moodie, R.B.² Schofield, K.³ Weston, J.B.⁴ Coombes, R.G.⁵ Golding, J.G.⁶ Tobin, G.D.⁷

31
- 0013543059
- (a) Halvarson, K.; Melander, L. Arkiv. Kemi 1957, 11, 77.
- (1957) Arkiv. Kemi , vol.11 , pp. 77
- Halvarson, K.¹ Melander, L.²

32
- 7144250735
- (b) Kovacic, P.; Hiller, J. J., Jr. J. Org. Chem. 1965, 30, 2871.
- (1965) J. Org. Chem. , vol.30 , pp. 2871
- Kovacic, P.¹ Hiller Jr., J.J.²

33
- 7144226157
- (c) Brandt, L.; Verbesselt, R. Tetrahedron 1972,28, 89.
- (1972) Tetrahedron , vol.28 , pp. 89
- Brandt, L.¹ Verbesselt, R.²

34
- 37049139713
- (d) Norman, R. O. C.; Parr, W. J. E.; Thomas, C. B. J. Chem. Soc., Perkin Trans 1 1974, 369.
- (1974) J. Chem. Soc., Perkin Trans , vol.1 , pp. 369
- Norman, R.O.C.¹ Parr, W.J.E.² Thomas, C.B.³

35
- 37049070302
- (e) Suzuki, H.; Murashima, T.; Mori, T. J. Chem. Soc., Chem. Commun. 1994, 1443.
- (1994) J. Chem. Soc., Chem. Commun. , pp. 1443
- Suzuki, H.¹ Murashima, T.² Mori, T.³

36
- 0003873242
- For a summary of general analytical procedures, see: Strazzolini, P.; Giumanini, A. G.; Verardo, G. Bull. Chem. Soc. Jpn. 1996, 69, 2943.
- (1996) Bull. Chem. Soc. Jpn. , vol.69 , pp. 2943
- Strazzolini, P.¹ Giumanini, A.G.² Verardo, G.³

37
- 0006130886
- (a) Solladiè-Cavallo, A.; Csaky, A. G. J. Org. Chem. 1994, 59, 2585.
- (1994) J. Org. Chem. , vol.59 , pp. 2585
- Solladiè-Cavallo, A.¹ Csaky, A.G.²

38
- 37049088467
- (b) Barton, P.; Laws, A. P.; Page, M. I. J. Chem. Soc., Perkin Trans. 2 1994, 2021.
- (1994) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 2021
- Barton, P.¹ Laws, A.P.² Page, M.I.³

39
- 0000498616
- (a) Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1981, 46, 4327.
- (1981) J. Org. Chem. , vol.46 , pp. 4327
- Bordwell, F.G.¹ Fried, H.E.²

40
- 84986870305
- (b) Orsini, F.; Severini Ricca, G. Org. Magn. Reson. 1984, 22, 653.
- (1984) Org. Magn. Reson. , vol.22 , pp. 653
- Orsini, F.¹ Severini Ricca, G.²

41
- 0345143099
- Taylor, R. J. Chem. Soc., Perkin Trans. 2 1975, 1025.
- (1975) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1025
- Taylor, R.¹

42
- 0001301330
- (a) Inaba, S.; Rieke, R. D. J. Org. Chem. 1985, 50, 1373.
- (1985) J. Org. Chem. , vol.50 , pp. 1373
- Inaba, S.¹ Rieke, R.D.²

43
- 0026697583
- (b) Rivière-Baudet, M.; Morère, A.; Dias, M. Tetrahedron Lett. 1992, 33, 6453.
- (1992) Tetrahedron Lett , vol.33 , pp. 6453
- Rivière-Baudet, M.¹ Morère, A.² Dias, M.³

44
- 0037602668
- (a) Baldwin, J. E.; Adlington, R. M.; Bottaro, J. C.; Kolhe, J. N.; Perry, M. W. D.; Jain, A. U. Tetrahedron 1986, 42, 4223.
- (1986) Tetrahedron , vol.42 , pp. 4223
- Baldwin, J.E.¹ Adlington, R.M.² Bottaro, J.C.³ Kolhe, J.N.⁴ Perry, M.W.D.⁵ Jain, A.U.⁶

45
- 0000882374
- (b) Katritzky, A. R.; Yang, Z.; Lam, J. N. J. Org. Chem. 1991, 56, 6917.
- (1991) J. Org. Chem. , vol.56 , pp. 6917
- Katritzky, A.R.¹ Yang, Z.² Lam, J.N.³

46
- 6444230041
- John Wiley & Sons, London, Coll.
- Julian, P. L.; Oliver, J. J. Organic Syntheses; John Wiley & Sons, London, 1943; Coll. Vol. 2, p 391.
- (1943) Organic Syntheses , vol.2 , pp. 391
- Julian, P.L.¹ Oliver, J.J.²

47
- 5844350938
- (a) Bradamante, S.; Pagani, G. A. J. Org. Chem. 1980, 45, 105.
- (1980) J. Org. Chem. , vol.45 , pp. 105
- Bradamante, S.¹ Pagani, G.A.²

48
- 0027419311
- (b) Ortiz, B.; Walls, F.; Yuste, F.; Barrios, H.; Sànchez-Obregòn, R.; Pinelo, L. Synth. Commun. 1993, 23, 749.
- (1993) Synth. Commun. , vol.23 , pp. 749
- Ortiz, B.¹ Walls, F.² Yuste, F.³ Barrios, H.⁴ Sànchez-Obregòn, R.⁵ Pinelo, L.⁶

49
- 37049100889
- (a) Brownlee, R. T. C.; Butt, G.; Chan, M. P.; Topsom, R. D. J. Chem. Soc., Perkin Trans. 2 1976, 1486.
- (1976) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1486
- Brownlee, R.T.C.¹ Butt, G.² Chan, M.P.³ Topsom, R.D.⁴

50
- 37049105031
- (b) Giordano, C.; Castaldi, G.; Casagrande, F.; Belli, A. J. Chem. Soc., Perkin Trans. 1 1982, 2575.
- (1982) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2575
- Giordano, C.¹ Castaldi, G.² Casagrande, F.³ Belli, A.⁴

51
- 0000159202
- (c) Hwu, J. R.; Wein, Y. S.; Leu, Y.-J. J. Org. Chem. 1996, 61, 1493.
- (1996) J. Org. Chem. , vol.61 , pp. 1493
- Hwu, J.R.¹ Wein, Y.S.² Leu, Y.-J.³

52
- 0001125871
- Ishikawa, H.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1978, 51, 2059.
- (1978) Bull. Chem. Soc. Jpn. , vol.51 , pp. 2059
- Ishikawa, H.¹ Mukaiyama, T.²

53
- 84943940048
- (a) Rüchardt, C.; Eichler, S. Chem. Ber. 1962, 95, 1921.
- (1962) Chem. Ber. , vol.95 , pp. 1921
- Rüchardt, C.¹ Eichler, S.²

54
- 0010934563
- (b) Norris, R. K.; Randles, D. Aust. J. Chem. 1979, 32, 1487.
- (1979) Aust. J. Chem. , vol.32 , pp. 1487
- Norris, R.K.¹ Randles, D.²

55
- 84980193659
- Tröndlin, F.; Werner, R.; Rüchardt, C. Chem. Ber. 1978, 111, 367.
- (1978) Chem. Ber. , vol.111 , pp. 367
- Tröndlin, F.¹ Werner, R.² Rüchardt, C.³

56
- 0001301160
- RajanBabu, T. V.; Chenard, B. L.; Petti, M. A. J. Org. Chem. 1986, 51, 1704.
- (1986) J. Org. Chem. , vol.51 , pp. 1704
- Rajanbabu, T.V.¹ Chenard, B.L.² Petti, M.A.³

57
- 0345924085
- Walter, M.; Besendorf, H.; Schnider, O. Helv. Chim. Acta 1963, 46, 1127.
- (1963) Helv. Chim. Acta , vol.46 , pp. 1127
- Walter, M.¹ Besendorf, H.² Schnider, O.³

58
- 84986980054
- Bowie, J. H.; Stapleton, B. J. Org. Mass Spectrom. 1977, 12, 436.
- (1977) Org. Mass Spectrom. , vol.12 , pp. 436
- Bowie, J.H.¹ Stapleton, B.J.²

59
- 27744591814
- Jönsson, N. Å.; Merenyi, F.; Svahn, C. M.; Gyllander, J. Acta Chem. Scand., Ser. B 1978, B 32, 317.
- (1978) Acta Chem. Scand., Ser. B , vol.B 32 , pp. 317
- Jönsson, N.Å.¹ Merenyi, F.² Svahn, C.M.³ Gyllander, J.⁴

60
- 0010649109
- Windholz, T. B. J. Org. Chem. 1960, 25, 1703.
- (1960) J. Org. Chem. , vol.25 , pp. 1703
- Windholz, T.B.¹

61
- 3242698936
- (a) Goetz, F. J.; Hirsch, J. A.; Augustine, R. L. J. Org. Chem. 1983, 48, 2468.
- (1983) J. Org. Chem. , vol.48 , pp. 2468
- Goetz, F.J.¹ Hirsch, J.A.² Augustine, R.L.³

62
- 0023889211
- (b) Lee, D.-U.; Mayer, K. K.; Wiegrebe, W. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 265.
- (1988) Arch. Pharm. (Weinheim, Ger.) , vol.321 , pp. 265
- Lee, D.-U.¹ Mayer, K.K.² Wiegrebe, W.³

63
- 0343371801
- (c) Makosza, M.; Sypniewski, M.; Glinka, T. Tetrahedron 1996, 52, 3189.
- (1996) Tetrahedron , vol.52 , pp. 3189
- Makosza, M.¹ Sypniewski, M.² Glinka, T.³

64
- 0023891057
- Lee, D.-U.; Mayer, K. K.; Wiegrebe, W. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 315.
- (1988) Arch. Pharm. (Weinheim, Ger.) , vol.321 , pp. 315
- Lee, D.-U.¹ Mayer, K.K.² Wiegrebe, W.³

65
- 84920290647
- Jaenisch, A. Chem. Ber. 1923, 56, 56B, 2448.
- (1923) Chem. Ber. , vol.56 , Issue.56 B , pp. 2448
- Jaenisch, A.¹

66
- 84920303300
- Zemplén, G.; Csürös, Z.; Gerecs, Å.; Aczél, S. Chem. Ber. 1928, 61, 61B, 2486.
- (1928) Chem. Ber. , vol.61 , Issue.61 B , pp. 2486
- Zemplén, G.¹ Csürös, Z.² Gerecs, Å.³ Aczél, S.⁴

67
- 0000581832
- Raucher, S.; Koolpe, G. A. J. Org. Chem. 1983, 48, 2066.
- (1983) J. Org. Chem. , vol.48 , pp. 2066
- Raucher, S.¹ Koolpe, G.A.²

68
- 0027090054
- Striegel, H.-G.; Mayer, K. K.; Wiegrebe, W. Arch. Pharm. (Weinheim, Ger.) 1992, 325, 751.
- (1992) Arch. Pharm. (Weinheim, Ger.) , vol.325 , pp. 751
- Striegel, H.-G.¹ Mayer, K.K.² Wiegrebe, W.³

69
- 2442728303
- Bakke, J. Acta Chem. Scand., Ser. B 1974, B 28, 134.
- (1974) Acta Chem. Scand., Ser. B , vol.B 28 , pp. 134
- Bakke, J.¹

70
- 0000360166
- Molina, P.; Alajarín, M.; Sánchez-Andrada, P. J. Org. Chem. 1996, 61, 4289.
- (1996) J. Org. Chem. , vol.61 , pp. 4289
- Molina, P.¹ Alajarín, M.² Sánchez-Andrada, P.³

71
- 21844502758
- Siemeling, U.; Türk, T.; Hammermeister, U. Monatsh. Chem. 1995, 126, 725.
- (1995) Monatsh. Chem. , vol.126 , pp. 725
- Siemeling, U.¹ Türk, T.² Hammermeister, U.³

72
- 0037957863
- Saunders, D. G. Synthesis 1988, 377.
- (1988) Synthesis , pp. 377
- Saunders, D.G.¹

73
- 0010361508
- Yabroff, D. L.; Porter, C. W. J. Am. Chem. Soc. 1932, 54, 2507.
- (1932) J. Am. Chem. Soc. , vol.54 , pp. 2507
- Yabroff, D.L.¹ Porter, C.W.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.