SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5800-5803

Aminolysis of Y-substituted phenyl X-substituted benzoates with piperidine: Effect of nonleaving group substituent

(4) Um, Ik Hwan a Lee, Ji Youn a Ko, Seung Hak b Bae, Sun Kun b

a Ewha Womans University (South Korea)

b Kunsan National University (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DECOMPOSITION; DERIVATIVES; NITROGEN COMPOUNDS; RATE CONSTANTS; SUBSTITUTION REACTIONS;

AMINOLYSIS; BENZOATES; BENZOYL MOIETY; ZWITTERIONIC TETRAHEDRAL INTERMEDIATE;

BENZENE;

BENZOIC ACID DERIVATIVE; PHENYL GROUP; PIPERIDINE DERIVATIVE;

AMINOLYSIS; ARTICLE; CHEMICAL REACTION KINETICS; ELECTRON MICROSCOPY; PKA; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 33746352814 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0606958 Document Type: Article

Times cited : (77)

References (53)

1
- 3042520570
- (a) Jencks, W. P. Chem. Rev. 1985, 85, 511-527.
- (1985) Chem. Rev. , vol.85 , pp. 511-527
- Jencks, W.P.¹

2
- 0000643086
- (b) Castro, E. A. Chem. Rev. 1999, 99, 3505-3524.
- (1999) Chem. Rev. , vol.99 , pp. 3505-3524
- Castro, E.A.¹

3
- 0003841848
- Longman: Harlow, UK, Ch. 7
- (c) Page, M. I.; Williams, A. Organic and Bio-organic Mechanisms; Longman: Harlow, UK, 1997; Ch. 7.
- (1997) Organic and Bio-organic Mechanisms
- Page, M.I.¹ Williams, A.²

4
- 22144451481
- (a) Oh, H. K.; Oh, J. Y.; Sung, D. D.; Lee, I. J. Org. Chem. 2005, 70, 5624-5629.
- (2005) J. Org. Chem. , vol.70 , pp. 5624-5629
- Oh, H.K.¹ Oh, J.Y.² Sung, D.D.³ Lee, I.⁴

5
- 1942421616
- (b) Lee, I.; Sung, D. D. Curr. Org. Chem. 2004, 8, 557-567.
- (2004) Curr. Org. Chem. , vol.8 , pp. 557-567
- Lee, I.¹ Sung, D.D.²

6
- 10844263408
- (c) Oh, H. K.; Park, J. E.; Sung, D. D.; Lee, I. J. Org. Chem. 2004, 69, 9285-9288.
- (2004) J. Org. Chem. , vol.69 , pp. 9285-9288
- Oh, H.K.¹ Park, J.E.² Sung, D.D.³ Lee, I.⁴

7
- 9344239382
- (d) Oh, H. K.; Ha, J. S.; Sung, D. D.; Lee, I. J. Org. Chem. 2004, 69, 8219-8223.
- (2004) J. Org. Chem. , vol.69 , pp. 8219-8223
- Oh, H.K.¹ Ha, J.S.² Sung, D.D.³ Lee, I.⁴

8
- 2542480172
- (e) Oh, H. K.; Lee, J. M.; Sung, D. D.; Lee, I. Bull. Korean Chem. Soc. 2004, 25, 557-559.
- (2004) Bull. Korean Chem. Soc. , vol.25 , pp. 557-559
- Oh, H.K.¹ Lee, J.M.² Sung, D.D.³ Lee, I.⁴

9
- 31344471493
- (a) Um, I. H.; Jeon, S. E.; Seok, J. A. Chem.-Eur. J. 2006, 12, 1237-1243.
- (2006) Chem.-Eur. J. , vol.12 , pp. 1237-1243
- Um, I.H.¹ Jeon, S.E.² Seok, J.A.³

10
- 0141543645
- (b) Um, I. H.; Seok, J. A.; Kim, H. T.; Bae, S. K. J. Org. Chem. 2003, 68, 7742-7746.
- (2003) J. Org. Chem. , vol.68 , pp. 7742-7746
- Um, I.H.¹ Seok, J.A.² Kim, H.T.³ Bae, S.K.⁴

11
- 33947090820
- (c) Menger, F. M.; Smith, J. H. J. Am. Chem. Soc. 1972, 94, 3824-3829.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 3824-3829
- Menger, F.M.¹ Smith, J.H.²

12
- 17044428979
- (a) Castro, E. A.; Aliaga, M.; Santos, J. G. J. Org. Chem. 2005, 70, 2679-2685.
- (2005) J. Org. Chem. , vol.70 , pp. 2679-2685
- Castro, E.A.¹ Aliaga, M.² Santos, J.G.³

13
- 25444437992
- (b) Castro, E. A.; Gazitua, M.; Santos, J. G. J. Org. Chem. 2005, 70, 8088-8092.
- (2005) J. Org. Chem. , vol.70 , pp. 8088-8092
- Castro, E.A.¹ Gazitua, M.² Santos, J.G.³

14
- 4644279294
- (c) Castro, E. A.; Aliaga, M.; Santos, J. G. J. Org. Chem. 2004, 69, 6711-6714.
- (2004) J. Org. Chem. , vol.69 , pp. 6711-6714
- Castro, E.A.¹ Aliaga, M.² Santos, J.G.³

15
- 3042780036
- (d) Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 2004, 69, 4802-4807.
- (2004) J. Org. Chem. , vol.69 , pp. 4802-4807
- Castro, E.A.¹ Cubillos, M.² Santos, J.G.³

16
- 1842556422
- (e) Castro, E. A.; Cubillos, M.; Aliaga, M.; Evangelisti, S.; Santos, J. G. J. Org. Chem. 2004, 69, 2411-2416.
- (2004) J. Org. Chem. , vol.69 , pp. 2411-2416
- Castro, E.A.¹ Cubillos, M.² Aliaga, M.³ Evangelisti, S.⁴ Santos, J.G.⁵

17
- 2442645211
- (a) Um, I. H.; Kim, K. H.; Park, H. R.; Fujio, M.; Tsuno, Y. J. Org. Chem. 2004, 69, 3937-3942.
- (2004) J. Org. Chem. , vol.69 , pp. 3937-3942
- Um, I.H.¹ Kim, K.H.² Park, H.R.³ Fujio, M.⁴ Tsuno, Y.⁵

18
- 0033306509
- (b) Um, I. H.; Min, J. S.; Lee, H. W. Can. J. Chem. 1999, 77, 659-666.
- (1999) Can. J. Chem. , vol.77 , pp. 659-666
- Um, I.H.¹ Min, J.S.² Lee, H.W.³

19
- 2142650657
- (c) Um, I. H.; Chun, S. M.; Chae, O. M.; Fujio, M.; Tsuno, Y. J. Org. Chem. 2004, 69, 3166-3172.
- (2004) J. Org. Chem. , vol.69 , pp. 3166-3172
- Um, I.H.¹ Chun, S.M.² Chae, O.M.³ Fujio, M.⁴ Tsuno, Y.⁵

20
- 0038548286
- (d) Um, I. H.; Hong, J. Y.; Kim, J. J.; Chae, O. M.; Bae, S. K. J. Org. Chem. 2003, 68, 5180-5185.
- (2003) J. Org. Chem. , vol.68 , pp. 5180-5185
- Um, I.H.¹ Hong, J.Y.² Kim, J.J.³ Chae, O.M.⁴ Bae, S.K.⁵

21
- 13844306888
- (e) Um, I. H.; Hong, J. Y.; Seok, J. A. J. Org. Chem. 2005, 70, 1438-1444.
- (2005) J. Org. Chem. , vol.70 , pp. 1438-1444
- Um, I.H.¹ Hong, J.Y.² Seok, J.A.³

22
- 33645032588
- (a) Um, I. H.; Kim, E. J.; Park, H. R.; Jeon, S. E. J. Org. Chem. 2006, 71, 2302-2306.
- (2006) J. Org. Chem. , vol.71 , pp. 2302-2306
- Um, I.H.¹ Kim, E.J.² Park, H.R.³ Jeon, S.E.⁴

23
- 4644223589
- (b) Um, I. H.; Han, H. J.; Baek, M. H.; Bae, S. K. J. Org. Chem. 2004, 69, 6365-6370.
- (2004) J. Org. Chem. , vol.69 , pp. 6365-6370
- Um, I.H.¹ Han, H.J.² Baek, M.H.³ Bae, S.K.⁴

24
- 0037073828
- (c) Um, I. H.; Lee, S. E.; Kwon, H. J. J. Org. Chem. 2002, 67, 8999-9005.
- (2002) J. Org. Chem. , vol.67 , pp. 8999-9005
- Um, I.H.¹ Lee, S.E.² Kwon, H.J.³

25
- 20844448745
- (a) Um, I. H.; Lee, J. Y.; Lee, H. W.; Nagano, Y.; Fujio, M.; Tsuno, Y. J. Org. Chem. 2005, 70, 4980-4987.
- (2005) J. Org. Chem. , vol.70 , pp. 4980-4987
- Um, I.H.¹ Lee, J.Y.² Lee, H.W.³ Nagano, Y.⁴ Fujio, M.⁵ Tsuno, Y.⁶

26
- 0033835585
- (b) Um, I. H.; Min, J. S.; Ahn, J. A.; Hahn, H. J. J. Org. Chem. 2000, 65, 5659-5663.
- (2000) J. Org. Chem. , vol.65 , pp. 5659-5663
- Um, I.H.¹ Min, J.S.² Ahn, J.A.³ Hahn, H.J.⁴

27
- 0042936680
- Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6970-6980.
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 6970-6980
- Gresser, M.J.¹ Jencks, W.P.²

28
- 33845379426
- (a) Castro, E. A.; Santander, C. L. J. Org. Chem. 1985, 50, 3595-3600.
- (1985) J. Org. Chem. , vol.50 , pp. 3595-3600
- Castro, E.A.¹ Santander, C.L.²

29
- 33845375500
- (b) Castro, E. A.; Valdivia, J. L. J. Org. Chem. 1986, 51, 1668-1672.
- (1986) J. Org. Chem. , vol.51 , pp. 1668-1672
- Castro, E.A.¹ Valdivia, J.L.²

30
- 37049106440
- (c) Castro, E. A.; Steinfort, G. B. J. Chem. Soc., Perkin Trans. 2 1983, 453-457.
- (1983) J. Chem. Soc., Perkin Trans. 2 , pp. 453-457
- Castro, E.A.¹ Steinfort, G.B.²

31
- 24944539627
- (a) Castro, E. A.; Aguayo, R.; Bessolo, J.; Santos, J. G. J. Org. Chem. 2005, 70, 7788-7791.
- (2005) J. Org. Chem. , vol.70 , pp. 7788-7791
- Castro, E.A.¹ Aguayo, R.² Bessolo, J.³ Santos, J.G.⁴

32
- 17744367257
- (b) Castro, E. A.; Aguayo, R.; Bessolo, J.; Santos, J. G. J. Org. Chem. 2005, 70, 3530-3536.
- (2005) J. Org. Chem. , vol.70 , pp. 3530-3536
- Castro, E.A.¹ Aguayo, R.² Bessolo, J.³ Santos, J.G.⁴

33
- 3542994464
- (c) Castro, E. A.; Vivanco, M.; Aguayo, R.; Aguayo, R.; Santos, J. G. J. Org. Chem. 2004, 69, 5399-5404.
- (2004) J. Org. Chem. , vol.69 , pp. 5399-5404
- Castro, E.A.¹ Vivanco, M.² Aguayo, R.³ Aguayo, R.⁴ Santos, J.G.⁵

34
- 0142090142
- (d) Castro, E. A.; Aguayo, R.; Santos, J. G. J. Org. Chem. 2003, 68, 8157-8161.
- (2003) J. Org. Chem. , vol.68 , pp. 8157-8161
- Castro, E.A.¹ Aguayo, R.² Santos, J.G.³

35
- 0003595276
- Brooks/Cole: New York
- (a) Carrol, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole: New York, 1998: pp 371-386.
- (1998) Perspectives on Structure and Mechanism in Organic Chemistry , pp. 371-386
- Carrol, F.A.¹

36
- 0003887404
- Harper Collins Publishers: New York
- (b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper Collins Publishers: New York, 1987; pp 143-151.
- (1987) Mechanism and Theory in Organic Chemistry, 3rd Ed. , pp. 143-151
- Lowry, T.H.¹ Richardson, K.S.²

37
- 33847090104
- Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963-6970.
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 6963-6970
- Gresser, M.J.¹ Jencks, W.P.²

38
- 0346136017
- (a) Lee, I. Chem. Soc. Rev. 1995, 223-229.
- (1995) Chem. Soc. Rev. , pp. 223-229
- Lee, I.¹

39
- 0033993075
- (b) Oh, H. K.; Yang, J. H.; Sung, D. D.; Lee, I. J. Chem. Soc., Perkin Trans. 2 2000, 101-105.
- (2000) Chem. Soc., Perkin Trans. 2 , pp. 101-105
- Oh, H.K.¹ Yang, J.H.² Sung, D.D.³ Lee, I.J.⁴

40
- 0034686679
- Swansburg, S.; Buncel, E.; Lemieux, R. P. J. Am. Chem. Soc. 2000, 122, 6594-6600.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 6594-6600
- Swansburg, S.¹ Buncel, E.² Lemieux, R.P.³

41
- 1842451690
- (a) Um, I. H.; Lee, J. Y.; Kim, H. T.; Bae, S. K. J. Org. Chem. 2004, 69, 2436-2441.
- (2004) J. Org. Chem. , vol.69 , pp. 2436-2441
- Um, I.H.¹ Lee, J.Y.² Kim, H.T.³ Bae, S.K.⁴

42
- 0037195670
- (b) Um, I. H.; Hahn, H. J.; Ahn, J. A.; Kang, S.; Buncel, E. J. Org. Chem. 2002, 67, 8475-8480.
- (2002) J. Org. Chem. , vol.67 , pp. 8475-8480
- Um, I.H.¹ Hahn, H.J.² Ahn, J.A.³ Kang, S.⁴ Buncel, E.⁵

43
- 0000854145
- Cevasco, G.; Guanti, G.; Hopkins, A. R.; Thea, S.; Williams, A. J. Org. Chem. 1985, 50, 479-484.
- (1985) J. Org. Chem. , vol.50 , pp. 479-484
- Cevasco, G.¹ Guanti, G.² Hopkins, A.R.³ Thea, S.⁴ Williams, A.⁵

44
- 0000497557
- (a) Tsuno, Y.; Fujio, M. Adv. Phys. Org. Chem. 1999, 32, 267-385.
- (1999) Adv. Phys. Org. Chem. , vol.32 , pp. 267-385
- Tsuno, Y.¹ Fujio, M.²

45
- 0030520758
- (b) Tsuno, Y.; Fujio, M. Chem. Soc. Rev. 1996, 25, 129-139.
- (1996) Chem. Soc. Rev. , vol.25 , pp. 129-139
- Tsuno, Y.¹ Fujio, M.²

46
- 0037250133
- (a) Fujio, M.; Rappoport, Z.; Uddin, M. K.; Kim, H. J.; Tsuno, Y. Bull. Chem. Soc. Jpn. 2003, 76, 163-169.
- (2003) Bull. Chem. Soc. Jpn. , vol.76 , pp. 163-169
- Fujio, M.¹ Rappoport, Z.² Uddin, M.K.³ Kim, H.J.⁴ Tsuno, Y.⁵

47
- 0038274881
- (b) Nakata, K.; Fujio, M.; Nishimoto, K.; Tsuno, Y. J. Phys. Org. Chem. 2003, 16, 323-335.
- (2003) J. Phys. Org. Chem. , vol.16 , pp. 323-335
- Nakata, K.¹ Fujio, M.² Nishimoto, K.³ Tsuno, Y.⁴

48
- 33947303518
- (a) Kirsch, J. F.; Clewell, W.; Simon, A. J. Org. Chem. 1968, 33, 127-132.
- (1968) J. Org. Chem. , vol.33 , pp. 127-132
- Kirsch, J.F.¹ Clewell, W.² Simon, A.³

49
- 33947489184
- (b) Kirsch, J. F.; Jencks, W. P. J. Am. Chem. Soc. 1964, 86, 837-846.
- (1964) J. Am. Chem. Soc. , vol.86 , pp. 837-846
- Kirsch, J.F.¹ Jencks, W.P.²

50
- 0015517234
- (a) Hubbard, C. D.; Kirsch, J. F. Biochemistry, 1972, 11, 2483-2493.
- (1972) Biochemistry , vol.11 , pp. 2483-2493
- Hubbard, C.D.¹ Kirsch, J.F.²

51
- 0011807154
- (b) Akahori, Y. Chem. Pharm. Bull. 1965, 13, 368-378.
- (1965) Chem. Pharm. Bull. , vol.13 , pp. 368-378
- Akahori, Y.¹

52
- 0011878091
- (c) Hashimoto, S.; Furukawa, I. Bull. Chem. Soc. Jpn. 1981, 54, 2227-2228.
- (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 2227-2228
- Hashimoto, S.¹ Furukawa, I.²

53
- 0035813305
- (d) Chakraborti, A. K.; Sharma, L.; Sharma, U. Tetrahedron 2001, 57, 9343-9346.
- (2001) Tetrahedron , vol.57 , pp. 9343-9346
- Chakraborti, A.K.¹ Sharma, L.² Sharma, U.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.