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TTF-containing macrocyclic compounds have been synthesized in most cases by using a coupling reaction in the presence of trialkyl phosphites from the corresponding thiones (see ref. [11] and [13]). There are only few reports describing the synthesis of TTF-derived macrocyclic systems directly starting from TTF-containing precursors (see ref. [11 a]).
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Some of the results discussed in this paper have been mentioned in a preliminary communication
-
Some of the results discussed in this paper have been mentioned in a preliminary communication: Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719;
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Li, Z.-T.1
Stein, P.C.2
Svenstrup, N.3
Lund, K.H.4
Becher, J.5
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83
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84891329149
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-
note
-
This chain had been proved suitable for preparing a 1,4-dioxyphenylene- based rotaxane (see ref. [6b]).
-
-
-
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84
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84982058045
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A. Lüttringhaus, F. Cramer, H. Prinzbach, F. M. Henglein, Liebigs Am. Chem. 1958, 613, 185.
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Liebigs Am. Chem.
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Lüttringhaus, A.1
Cramer, F.2
Prinzbach, H.3
Henglein, F.M.4
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85
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0001363924
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A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215.
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(1983)
Tetrahedron Lett.
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Castellan, A.1
Daney, M.2
Desvergne, J.-P.3
Riffaud, M.-H.4
Bouas-Laurent, H.5
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86
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0027981950
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N. Svenstrup, K. M. Rasmussen, T. K. Hansen, J. Becher, Synthesis 1994, 809.
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(1994)
Synthesis
, pp. 809
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Svenstrup, N.1
Rasmussen, K.M.2
Hansen, T.K.3
Becher, J.4
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87
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84891318356
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-
note
-
The mixtures of isomers could not be separated because they slowly isomerized to each other in solution containing trace amounts of acid (detected by TLC). In all the reactions leading to the monomacrocyclic compounds 7a-d, no 2,3-deprotection-cyclization products were detected (TLC indicated that no other major products were formed except the insoluble linear oligomers), although tetrathiafulvalene-2,3,6,7-tetrathiolate could be produced quantitatively from 6 in the presence of 8 equiv of cesium hydroxide (see ref. [20]).
-
-
-
-
88
-
-
84891333105
-
-
note
-
1H NMR spectrum indicated that the ratio of the cis and trans isomers is about 5:1, based on the integration of the two phenylene proton signals.
-
-
-
-
89
-
-
84891331040
-
-
note
-
Recently, [2]catenanes incorporating a bis(2-oxy-1,3-propylenedithio) tetrathiafulvalene unit and a 1,4-bis(oxymethyl)phenylene unit have been synthesized by Prof. Stoddart's group. We thank Dr. G. Mattersteig and Prof. J. F. Stoddart for providing the information.
-
-
-
-
90
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0001666976
-
-
Ultra-high pressure has been used to promote the formation of catenanes; see
-
Ultra-high pressure has been used to promote the formation of catenanes; see D. B. Amabilino, P. R. Ashton, M. S. Tolley, J. F. Stoddart, D. J. Williams, Angew. Chem. 1993, 105, 1358;
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Angew. Chem.
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, pp. 1358
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Amabilino, D.B.1
Ashton, P.R.2
Tolley, M.S.3
Stoddart, J.F.4
Williams, D.J.5
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92
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84891302795
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-
note
-
Quantitative synthesis of [2]catenanes has been reported recently by utilizing the labile nature of a palladium or platinum(II)-pyridine coordinate bond, in which Pd or Pt metal centers are part of the macrocycles but do not intervene during the catenation (see ref. [4a]).
-
-
-
-
93
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84891284679
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note
-
Unsymmetrical TTF compounds usually isomerize readily, catalyzed by trace amounts of acid. Two methods have been used to control the configurational isomerization of TTF macrocyclic compounds. The first utilized the difference between the ring strains of the cis/trans isomers (see ref. [11c] and [13]). The second approach involved one-electron oxidation of [12]- and [14]tetrathiafulvalenophanes (see ref. [11 d]). However, in all these cases the planarity of the neutral TTF subunits was destroyed by the short chains linking the opposite ends of the TTF groups.
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-
-
-
94
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0000728385
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-
a) P. R. Ashton, C. L. Brown, E. J. T. Chrystal, T. T. Goodnow, A. E. Kaifer, K. P. Parry, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1991, 103, 1055;
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Ashton, P.R.1
Brown, C.L.2
Chrystal, E.J.T.3
Goodnow, T.T.4
Kaifer, A.E.5
Parry, K.P.6
Slawin, A.M.Z.7
Spencer, N.8
Stoddart, J.F.9
Williams, D.J.10
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96
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0000956295
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-
b) D. B. Amabilino, P. R. Ashton, A. S. Reder, N. Spencer, J. F. Stoddart, ibid. 1994, 106, 1316
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(1994)
Angew. Chem. Int. Ed. Engl.
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, pp. 1316
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Amabilino, D.B.1
Ashton, P.R.2
Reder, A.S.3
Spencer, N.4
Stoddart, J.F.5
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98
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0007513185
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-
c) P. R. Ashton, L. Peres-Garcia, J. F. Stoddart, A. J. P. White, D. J. Williams, ibid. 1995, 107, 607
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(1995)
Angew. Chem. Int. Ed. Engl.
, vol.107
, pp. 607
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Ashton, P.R.1
Peres-Garcia, L.2
Stoddart, J.F.3
White, A.J.P.4
Williams, D.J.5
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100
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0001746879
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-
d) M. J. Gunter, D. C. R. Hockless, M. R. Johnston, B. W. Skelton, A. H. White, J. Am. Chem. Soc. 1994, 116, 4810;
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 4810
-
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Gunter, M.J.1
Hockless, D.C.R.2
Johnston, M.R.3
Skelton, B.W.4
White, A.H.5
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101
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37049071283
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e) P. R. Ashton, R. Ballardini, V. Balzani, M. T. Gandolfi, D. J.-F. Marquis, L. Peres-Garcia, L. Prodi, J. F. Stoddart, M. Venturi, J. Chem. Soc. Chem. Commun. 1994, 177;
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(1994)
J. Chem. Soc. Chem. Commun.
, pp. 177
-
-
Ashton, P.R.1
Ballardini, R.2
Balzani, V.3
Gandolfi, M.T.4
Marquis, D.J.-F.5
Peres-Garcia, L.6
Prodi, L.7
Stoddart, J.F.8
Venturi, M.9
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102
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0009647674
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f) D. B. Amabilino, P. R. Ashton, J. F. Stoddart, S. Menzer, D. J. Williams, ibid. 1994, 2475.
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(1994)
J. Chem. Soc. Chem. Commun.
, pp. 2475
-
-
Amabilino, D.B.1
Ashton, P.R.2
Stoddart, J.F.3
Menzer, S.4
Williams, D.J.5
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103
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-
85069014694
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-
Constitutional changes may have great influence on the self-assembly of catenanes; see ref. [27a] and also
-
Constitutional changes may have great influence on the self-assembly of catenanes; see ref. [27a] and also D. B. Amabilino, P. R. Ashton, G. R. Brown, W. Hayes, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Chem. Soc. Chem. Commun. 1994, 2479.
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(1994)
J. Chem. Soc. Chem. Commun.
, pp. 2479
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-
Amabilino, D.B.1
Ashton, P.R.2
Brown, G.R.3
Hayes, W.4
Stoddart, J.F.5
Tolley, M.S.6
Williams, D.J.7
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104
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84891294761
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-
note
-
1H NMR spectra (based on the integration of the two sets of aromatic proton signals).
-
-
-
-
105
-
-
0026677020
-
-
5 +, have apparently not been reported previously; see
-
5 +, have apparently not been reported previously; see P. R. Ashton, C. L. Brown, J. R. Chapman, R. T. Gallagher, J. F. Stoddart, Tetrahedron Lett, 1992, 33, 7771.
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(1992)
Tetrahedron Lett
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Ashton, P.R.1
Brown, C.L.2
Chapman, J.R.3
Gallagher, R.T.4
Stoddart, J.F.5
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