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For a review: Diederich, F. Cyclophanes; The Royal Society of Chemistry: Cambridge, 1991.
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(a) Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
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(b) Tobe, Y.; Nakagawa, N.; Kishi, J.; Sonoda, M.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. Tetrahedron 2001, 57, 3629.
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A similar mechanism was proposed: Fallis, A. G. Can. J. Chem. 1999, 77, 159.
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Fallis, A.G.1
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60 was accomplished by flash vacuum pyrolysis of a polycyclic chlorinated hydrocarbon: Scott, L. T.; Boorum, M. M.; McMahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wagner, H.; de Meijere, A. Science 2002, 295, 1500.
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Mack, J.5
Blank, J.6
Wagner, H.7
De Meijere, A.8
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Tobe, Y.; Furukawa, R.; Sonoda, M.; Wakabayashi, T. Angew. Chem., Int. Ed. 2001, 40, 4072.
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12
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0034618555
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For representative examples for the formation of small carbon clusters from organic precursors: (a) Prinzbach, H.; Weiler, A.; Landenberger, P.; Wahl, F.; Worth, J.; Scott, L. T.; Gelmont, M.; Olevano, D.; Issendorff, B. v. Nature 2000, 407, 60. (b) Manini, P.; Amrein, W.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. 2002, 41, 4339.
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Prinzbach, H.1
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Landenberger, P.3
Wahl, F.4
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Scott, L.T.6
Gelmont, M.7
Olevano, D.8
Issendorff, B.V.9
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13
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0037112596
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For representative examples for the formation of small carbon clusters from organic precursors: (a) Prinzbach, H.; Weiler, A.; Landenberger, P.; Wahl, F.; Worth, J.; Scott, L. T.; Gelmont, M.; Olevano, D.; Issendorff, B. v. Nature 2000, 407, 60. (b) Manini, P.; Amrein, W.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. 2002, 41, 4339.
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Manini, P.1
Amrein, W.2
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Diederich, F.4
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14
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0344341202
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note
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Compounds 3a, 3b, and 4 were unseparable mixtures of diastereomers, of which one isomer is drawn for clarity.
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15
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0029769640
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2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
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Kawase, T.1
Ueda, N.2
Darabi, H.R.3
Oda, M.4
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16
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0030767549
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2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
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Kawase, T.1
Ueda, N.2
Oda, M.3
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17
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0033245546
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2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
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Chem. Lett.
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Kawase, T.1
Hosokawa, Y.2
Kurata, H.3
Oda, M.4
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18
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0035823729
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2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
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Chem. Commun.
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Hosokawa, Y.1
Kawase, T.2
Oda, M.3
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Shultz, D. A.; Lee, H.; Kumar, R. K.; Gwaltney, K. P. J. Org. Chem. 1999, 64, 9124.
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Shultz, D.A.1
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21
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(b) Lavastre, O.; Cabioch, S.; Dixneuf, P. H.; Vohlidal, J. Tetrahedron 1997, 53 7595.
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Vohlidal, J.4
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22
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0345635614
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note
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The lowest-field signal of 6 which appeared at 152 ppm was due to the aromatic carbon attached to the tert-butyl group.
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23
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0002577139
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(a) Similar deshielding effect was observed in a [8]metacyclophanedienediyne system: Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2002, 4, 11.
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Org. Lett.
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Collins, S.K.1
Yap, G.P.A.2
Fallis, A.G.3
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24
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0344773069
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note
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w = 0.188.
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25
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0000831766
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Halton, B., Ed.; JAI Press: Greenwich
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For the definition of the deformations angles of strained cyclophanes, see: Bickelhaupt, F.; de Wolf, W. H. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: Greenwich, 1993; Vol. 3, p 185.
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(1993)
Advances in Strain in Organic Chemistry
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Bickelhaupt, F.1
De Wolf, W.H.2
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26
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1842408893
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(a) Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052.
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Boese, R.1
Matzger, A.J.2
Vollhardt, K.P.C.3
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27
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0000709073
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(b) Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215.
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Baldwin, K.P.1
Matzger, A.J.2
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Tessier, C.A.4
Vollhardt, K.P.C.5
Youngs, W.J.6
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28
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0345203631
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note
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For the corresponding cyclobutenyl case, see refs 3 and 4.
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29
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0034677083
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(a) Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Angew. Chem., Int. Ed. 2000, 39, 385.
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Angew. Chem., Int. Ed.
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Collins, S.K.1
Yap, G.P.A.2
Fallis, A.G.3
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0001516858
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(b) Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2000, 2, 3189.
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Org. Lett.
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Collins, S.K.1
Yap, G.P.A.2
Fallis, A.G.3
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31
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0344773072
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note
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For the corresponding cyclobutenyl case, see ref 7.
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34
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37049057697
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(b) Behr, O. M.; Eglinton, G.; Galbraith, A. R.; Raphael, R. A. J. Chem. Soc. 1960, 3614.
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Behr, O.M.1
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Raphael, R.A.4
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