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Journal of Organic Chemistry

Volumn 66, Issue 10, 2001, Pages 3265-3276

Radical cation ester cleavage in solution. Mechanism of the mesolytic O-CO bond scission

(5) Schmittel, M a Peters, K b Peters, E M b Haeuseler, A a Trenkle, H c

a UNIVERSITY OF SIEGEN (Germany)

b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG (Germany)

c UNIVERSITY OF WÜRZBURG (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ONE-ELECTRON OXIDANTS;

ANODIC OXIDATION; CYCLIC VOLTAMMETRY; ESTERS; SPECTROSCOPY;

ORGANIC COMPOUNDS;

BENZOFURAN DERIVATIVE; CARBAMIC ACID ESTER; CARBONIC ACID DERIVATIVE; CATION; ESTER;

ARTICLE; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTRON SPIN RESONANCE; KINETICS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMODYNAMICS; X RAY ANALYSIS;

EID: 0035906485 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0057093 Document Type: Article

Times cited : (11)

References (115)

1
- 0004122810
- Balzani, V., Ed.; Wiley-VCH: Weinheim, Chapter 2.1.1
- (2001) Electron Transfer in Chemistry , vol.2
- Schmittel, M.¹ Ghorai, M.K.²

2
- 0003402416
- Wiley-VCH: Weinheim
- (1998) Radikale und Radikalionen in der Organischen Synthese
- Linker, T.¹ Schmittel, M.²

3
- 0002253358
- (1998) Chem. Soc. Rev. , vol.27 , pp. 81
- Mella, M.¹ Fagnoni, M.² Freccero, M.³ Fasani, E.⁴ Albini, A.⁵

4
- 33847087263
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7566
- Shaefer, C.G.¹ Peters, K.S.²

5
- 0000725558
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 7291
- Sinha, A.¹ Bruice, T.C.²

6
- 84931485849
- (1986) Z. Naturforsch. , vol.41 b , pp. 505
- Das, S.¹ Von Sonntag, C.²

7
- 0001911765
- (1986) Acc. Chem. Res. , vol.19 , pp. 401
- Lewis, F.D.¹

8
- 0001635342
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 2872
- Bordwell, F.G.¹ Cheng, J.-P.² Bausch, M.J.³

9
- 33845184897
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1792
- Bordwell, F.G.¹ Cheng, J.-P.²

10
- 0024843596
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8646
- Dinnocenzo, J.P.¹ Banach, T.E.²

11
- 0025317253
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 1337
- Hapiot, P.¹ Moiroux, J.² Savéant, J.-M.³

12
- 84987038467
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 1431
- Xu, W.¹ Mariano, P.S.²

13
- 0001397272
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 8863
- Xu, W.¹ Zhang, X.-M.² Mariano, P.S.³

14
- 0000980070
- (1991) J. Phys. Chem. , vol.95 , pp. 2370
- Anne, A.¹ Hapiot, P.² Moiroux, J.³ Neta, P.⁴ Savéant, J.-M.⁵

15
- 0003671961
- (1992) Chem. Phys. Lett. , vol.199 , pp. 409
- Tripathi, G.N.R.¹

16
- 0000885217
- (1992) J. Am. Chem. Soc. , vol.112 , pp. 4694
- Anne, A.¹ Hapiot, P.² Moiroux, J.³ Neta, P.⁴ Savéant, J.-M.⁵

17
- 0000335432
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 10173
- Bordwell, F.G.¹ Satish, A.V.²

18
- 0027891923
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 12290
- Baciocchi, E.¹ Del Giacco, T.² Elisei, F.³

19
- 0001373350
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11123
- Goez, M.¹ Sartorius, I.²

20
- 0003555462
- (1994) Chem. Ber. , vol.127 , pp. 2273
- Goez, M.¹ Sartorius, I.²

21
- 0031998193
- (1998) J. Phys. Chem. A , vol.102 , pp. 1457
- Brede, O.¹ Beckert, D.² Windolph, C.³ Göttinger, H.A.⁴

22
- 11744380034
- (1998) J. Phys. Chem. A , vol.102 , pp. 7337
- Bietti, M.¹ Baciocchi, E.² Steenken, S.³

23
- 0032539213
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 12720
- Parker, V.D.¹ Zhao, Y.X.² Lu, Y.³ Zheng, G.⁴

24
- 0000986317
- (1999) J. Phys. Org. Chem. , vol.12 , pp. 688
- Zhao, C.X.¹ Gong, Y.F.² He, H.Y.³ Jiang, X.K.⁴

25
- 0033017164
- (1999) Chem. Eur. J. , vol.5 , pp. 1785
- Baciocchi, E.¹ Bietti, M.² Steenken, S.³

26
- 33947094542
- (1978) J. Org. Chem. , vol.43 , pp. 4392
- Gassman, P.G.¹ Yamaguchi, R.² Koser, G.F.³

27
- 0000623860
- (1988) Tetrahedron Lett. , vol.29 , pp. 3635
- Penn, J.H.¹ Deng, D.-L.² Chai, K.-J.³

28
- 0000623860
- (1988) Tetrahedron Lett. , vol.29 , pp. 3635
- Penn, J.H.¹ Deng, D.-L.² Chai, K.-J.³

29
- 0001376980
- (1989) Can. J. Chem. , vol.67 , pp. 2119
- Arnold, D.R.¹ Lamont, L.J.²

30
- 0025082387
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 3068
- Popielarz, R.¹ Arnold, D.R.²

31
- 0000225118
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 9475
- Camaioni, D.M.¹

32
- 0000981072
- (1991) Can. J. Chem. , vol.69 , pp. 225
- Arnold, D.R.¹ Lamont, L.J.² Perrott, A.L.³

33
- 37049071288
- (1993) J. Chem. Soc., Perkin Trans. 2 , pp. 825
- Perrier, S.¹ Sankararaman, S.² Kochi, J.K.³

34
- 0000060065
- (1993) J. Phys. Chem. , vol.97 , pp. 9078
- Lucia, L.A.¹ Burton, R.D.² Schanze, K.S.³

35
- 0003626299
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 8038
- Leon, J.W.¹ Whitten, D.G.²

36
- 0001278859
- (1994) Angew. Chem. , vol.106 , pp. 110-113
- Maslak, P.¹ Vallombroso, T.M.² Chapman W.H., Jr.³ Narvaez, J.N.⁴

37
- 0002515097
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 73-75

38
- 0032556225
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 10676
- Su, Z.¹ Mariano, P.S.² Falvey, D.E.³ Yoon, U.C.⁴ Oh, S.W.⁵

39
- 0033448451
- (1999) Chem. Soc. Rev. , vol.28 , pp. 359
- Adam, W.¹ Heidenfelder, T.²

40
- 0024835737
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8973
- Dinnocenzo, J.P.¹ Farid, S.² Goodman, J.L.³ Gould, I.R.⁴ Todd, W.P.⁵ Mattes, S.L.⁶

41
- 0027275912
- (1993) Tetrahedron Lett. , vol.34 , pp. 2863
- Todd, W.P.¹ Dinnocenzo, J.P.² Farid, S.³ Goodman, J.L.⁴ Gould, A.L.⁵

42
- 0001434767
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 4211
- Zhang, X.¹ Yeh, S.-R.² Hong, S.³ Freccero, M.⁴ Albini, A.⁵ Falvey, D.E.⁶ Mariano, P.S.⁷

43
- 0033603218
- (1999) THEOCHEM , vol.466 , pp. 165
- Borosky, G.L.¹ Pierini, A.B.²

44
- 0001165744
- (1995) J. Org. Chem. , vol.60 , pp. 2726
- Schmittel, M.¹ Heinze, J.² Trenkle, H.³

45
- 0030728678
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10673
- Adam, W.¹ Kammel, T.² Toubartz, M.³ Steenken, S.⁴

46
- 37049074991
- (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 2327
- Schmittel, M.¹ Keller, M.² Burghart, A.³

47
- 0001426756
- (1996) J. Chem. Soc. Perlin Trans. 2 , pp. 1633
- Bockman, T.M.¹ Kochi, J.K.²

48
- 0033617164
- (1999) J. Org. Chem. , vol.64 , pp. 3077
- Schmittel, M.¹ Burghart, A.² Werner, H.³ Laubender, M.⁴ Söllner, R.⁵

49
- 0001401276
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 322
- Kohno, Y.¹ Narasaka, K.²

50
- 0026641501
- (1992) Tetrahedron , vol.48 , pp. 9483
- Sartori, G.¹ Maggi, R.² Bigi, F.³ Arienti, G.⁴ Casnati, G.⁵ Bocelli, G.⁶ Mori, G.⁷

51
- 0003696040
- (1996) Chem. Commun. , pp. 2349
- Schmittel, M.¹ Steffen, J.-P.² Burghart, A.³

52
- 0000104893
- (1999) Acta Chem. Scand. , vol.53 , pp. 781
- Schmittel, M.¹ Steffen, J.-P.² Burghart, A.³

53
- 0029848029
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2107
- Schmittel, M.¹ Söllner, R.²

54
- 0000436558
- (1997) Chem. Ber./Recueil , vol.130 , pp. 771
- Schmittel, M.¹ Söllner, R.²

55
- 0042241613
- (1998) Chem. Commun. , pp. 565
- Schmittel, M.¹ Söllner, R.²

56
- 0043136323
- (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 515
- Schmittel, M.¹ Söllner, R.²

57
- 4243905895
- (1998) Mendeleev Commun. , pp. 239
- Ogibin, Y.N.¹ Terent'ev, A.O.² Ilovaisky, A.I.³ Nikishin, G.I.⁴

58
- 0000969013
- (1994) J. Org. Chem. , vol.59 , pp. 5017
- Fry, A.J.¹ Little, R.D.² Leonetti, J.³

59
- 0000902322
- (1994) Chem. Ber. , vol.127 , pp. 1257
- Peek, R.¹ Streukens, M.² Thomas, H.G.³ Vanderfuhr, A.⁴ Wellen, U.⁵

60
- 0029683676
- (1996) J. Mass Spectrosc. , vol.31 , pp. 761
- Grossert, J.S.¹ Yhard, G.B.² Pincock, J.A.³ Curtis, J.M.⁴

61
- 0001166290
- (1995) Rapid Commun. Mass Spectrosc. , vol.9 , pp. 862
- Suh, D.¹ Burgers, P.C.² Terlouw, J.K.³

62
- 0025347575
- (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 283
- Maslak, P.¹ Narvaez, J.N.²

63
- 0000927384
- (1996) J. Chem. Soc., Perkin Trans. 2 , pp. 2401
- Schmittel, M.¹ Trenkle, H.²

64
- 0031515803
- (1997) Chem. Lett. , pp. 299
- Schmittel, M.¹ Trenkle, H.²

65
- 67650050863
- (1992) Chem. Ber. , vol.125 , pp. 1611
- Schmittel, M.¹ Röck, M.²

66
- 0001468117
- (1998) Perkin Trans. 2 , pp. 869
- Schmittel, M.¹ Keller, M.² Burghart, A.³ Rappoport, Z.⁴ Langels, A.⁵

67
- 33845282375
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 2122
- Nadler, E.B.¹ Rappoport, Z.²

68
- 22044445384
- (1998) Z. Kristallogr. , vol.213 , pp. 105
- Peters, K.¹ Peters, E.-M.² Schmittel, M.³ Trenkle, H.⁴

69
- 0003701056
- (1997) Z. Kristallogr. , vol.212 , pp. 467
- Peters, K.¹ Peters, E.-M.² Schmittel, M.³ Trenkle, H.⁴

70
- 33845185242
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8181
- Kaftory, M.¹ Nugiel, D.A.² Biali, S.E.³ Rappoport, Z.⁴

71
- 0003625843
- note

72
- 33744834506
- (1994) J. Prakt. Chem. , vol.336 , pp. 325
- Röck, M.¹ Schmittel, M.²

73
- 33748241922
- (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 541
- Schmittel, M.¹ Baumann, U.²

74
- 0003626304
- note

75
- 0021530170
- (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 831
- Heinze, J.¹

76
- 0003632919
- note

77
- 24444433905
- (1964) Anal. Chem. , vol.36 , pp. 6
- Nicholson, R.S.¹ Shain, I.²

78
- 0024835737
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8973
- Dinnocenzo, J.P.¹ Farid, S.² Goodman, J.L.³ Gould, I.R.⁴ Todd, W.P.⁵ Mattes, S.L.⁶

79
- 37049070781
- (1993) J. Chem. Soc., Chem. Commun. , pp. 1691
- Baciocchi, E.¹ Bernini, R.² Lanzalunga, O.³

80
- 0027275912
- (1993) Tetrahedron Lett. , vol.34 , pp. 2863
- Todd, W.P.¹ Dinnocenzo, J.P.² Farid, S.³ Goodman, J.L.⁴ Gould, I.R.⁵

81
- 0032567149
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11904
- Herbertz, T.¹ Roth, H.D.²

82
- 0032925601
- (1999) J. Org. Chem. , vol.64 , pp. 3708
- Herbertz, T.¹ Roth, H.D.²

83
- 0003705377
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6063
- Dinnocenzo, J.P.¹ Banach, T.E.²

84
- 0038378655
- (1997) Perkin Trans. 2 , pp. 2145
- Schmittel, M.¹ Gescheidt, G.² Eberson, L.³ Trenkle, H.⁴

85
- 0001362069
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 7686
- Sutcliffe, R.¹ Ingold, K.U.²

86
- 84892207703
- (1993) Acc. Chem. Res. , vol.26 , pp. 455
- Savéant, J.-M.¹

87
- 0033546675
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 7239
- Donkers, R.L.¹ Maran, F.² Wayner, D.D.M.³ Workentin, M.S.⁴

88
- 0003628017
- note

89
- 0842341771
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902
- Dewar, M.J.S.¹ Zoebisch, E.G.² Healy, E.F.³ Stewart, J.J.P.⁴

90
- 33845278203
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 132
- Wayner, D.D.M.¹ McPhee, D.J.² Griller, D.³

91
- 0000459993
- (1983) Acc. Chem. Res. , vol.16 , pp. 130
- Mariano, P.S.¹

92
- 0003713887
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 6439
- Lan, A.J.Y.¹ Quillen, S.L.² Heuckeroth, R.O.³ Mariano, P.S.⁴

93
- 0001991118
- (1992) Chem. Lett. , pp. 1995
- Yoshiyama, T.¹ Fuchigami, T.²

94
- 0001540319
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 4460
- Akaba, R.¹ Niimura, Y.² Fukushima, T.³ Kawai, Y.⁴ Tajima, T.⁵ Kuragami, T.⁶ Negishi, A.⁷ Kamata, M.⁸ Sakuragi, H.⁹ Tokumaru, K.¹⁰

95
- 0001434767
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 4211
- Zhang, X.¹ Yeh, S.-R.² Hong, S.³ Freccero, M.⁴ Albini, A.⁵ Falvey, D.E.⁶ Mariano, P.S.⁷

96
- 0000899672
- (1994) J. Org. Chem. , vol.59 , pp. 7190
- Fuchigami, T.¹ Fujita, T.²

97
- 0003589401
- (1995) J. Org. Chem. , vol.60 , pp. 2935
- Mizuno, K.¹ Tamai, T.² Hashida, I.³ Otsuji, Y.⁴

98
- 0031527772
- (1997) Chem. Lett. , pp. 161
- Fukuzumi, S.¹ Yasui, K.² Itoh, S.³

99
- 0031585117
- (1997) Tetrahedron , vol.53 , pp. 4469
- Baciocchi, E.¹ Crescenzi, C.² Lanzalunga, O.³

100
- 0032556225
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 10676
- Su, Z.¹ Mariano, P.S.² Falvey, D.E.³ Yoon, U.C.⁴ Oh, S.W.⁵

101
- 37049089027
- (1993) Chem. Commun. , pp. 1739
- Röck, M.¹ Schmittel, M.²

102
- 0000445778
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 1308
- Gassman, P.G.¹ Yamaguchi, R.²

103
- 33751499838
- (1991) J. Org. Chem. , vol.56 , pp. 4853
- Wayner, D.D.M.¹ Sim, B.A.² Dannenberg, J.J.³

104
- 0003625623
- note

105
- 0000628641
- (1993) Acc. Chem. Res. , vol.26 , pp. 287
- Wayner, D.D.M.¹ Parker, V.D.²

106
- 0003701060
- note

107
- 37049089027
- (1993) Chem. Commun. , pp. 1739
- Röck, M.¹ Schmittel, M.²

108
- 0000425333
- (1998) J. Org. Chem. , vol.63 , pp. 7328
- Schmittel, M.¹ Langels, A.²

109
- 0002269342
- (1989) J. Electroanal. Chem. Interfacial , vol.270 , pp. 43
- Amatore, C.¹ Lefrou, C.² Pflügler, F.³

110
- 4243976765
- (1966) Anal. Chem. , vol.38 , pp. 6
- Nicholson, R.S.¹

111
- 0020746677
- (1983) J. Electroanal. Chem. Interfacial Electrochem. , vol.146 , pp. 397
- Lasia, A.¹

112
- 0021423015
- (1984) J. Electroanal. Chem. Interfacial Electrochem. , vol.165 , pp. 61
- Heinze, J.¹ Störzbach, M.² Mortensen, J.³

113
- 0002591852
- (1993) J. Electroanal. Chem. Interfacial Electrochem. , vol.346 , pp. 1
- Heinze, J.¹ Störzbach, M.²

114
- 0028441766
- (1994) Anal. Chem. , vol.66
- Rudolph, M.¹ Reddy, D.P.² Feldberg, S.W.³

115
- 0001768454
- (1992) J. Electroanal. Chem. Interfacial Electrochem. , vol.338 , pp. 86
- Rudolph, M.¹

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