194
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Highly efficient synthesis of [3]rotaxane assisted by preorganisation of pseudorotaxane using bis(crown ether)s

, , &
Pages 815-826 | Received 31 May 2010, Accepted 22 Jul 2010, Published online: 15 Nov 2010

References

  • Amabilino , D.B. and Stoddart , J.F. 1995 . Chem. Rev. , 95 : 2725 – 2828 . (b) Pease, A.R.; Jeppesen, J.O.; Stoddart, J.F.; Luo, Y.; Collier, C.P.; Heath, J.R. Acc. Chem. Res. 2001, 34, 433–444
  • Harrison , T. and Harrison , S. 1967 . J. Am. Chem. Soc. , 89 : 5723 – 5724 .
  • Iijima , T. , Vignon , S.A. , Tseng , H.-R. , Jarrosson , T. , Sanders , J.K.M. , Marchioni , F. , Venturi , M. , Apostoli , E. , Balzani , V. and Stoddart , J.F. 2004 . Chem. Eur. J. , 10 : 6375 – 6392 . (b) Chambron, J.-C.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1993, 115, 12378–12384. (c) Anelli, P.L.; Ashton, P.R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M.T.; Goodnow, T.T.; Kaifer, A.E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M.V.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Vincent, C.; Williams, D.J. J. Am. Chem. Soc. 1992, 114, 193–218. (d) Anelli, P.L.; Spencer, N.; Stoddart, J.F. J. Am. Chem. Soc. 1991, 113, 5131–5133. (e) Ballardini, R.; Balzani, V.; Dehaen, W.; Dell'Erba, A.E.; Raymo, F.M.; Stoddart, J.F.; Venturi, M. Eur. J. Org. Chem. 2000, 65, 591–602. (f) Johnston, A.G.; Leigh, D.A.; Murphy, A.; Smart, J.P.; Deegan, M.D. J. Am. Chem. Soc. 1996, 118, 10662–10663. (g) Leigh, D.A.; Murphy, A.; Smart, J.P.; Slawin, A.M.Z. Angew. Chem. Int. Ed. Engl. 1997, 36, 728–732. (h) Gatti, F.G.; Leigh, D.A.; Nepogodiev, S.A.; Slawin, A.M.Z.; Teat, S.J.; Wong, J.K.Y. J. Am. Chem. Soc. 2001, 123, 5983–5989. (i) Bissell, A.; Córdova, E.; Kaifer, A.E.; Stoddart, J.F. Nature 1994, 369, 133–137. (j) Faviña, P.; Sauvage, J.-P. Tetrahedron Lett. 1997, 38, 3521–3524. (k) Collin, J.-P.; Faviña, P.; Sauvage, J.-P. New J. Chem. 1997, 21, 525–528. (l) Armaroli, N.; Balzani, V.; Collin, J.-P.; Faviña, P.; Sauvage, J.-P.; Ventura, B. J. Am. Chem. Soc. 1999, 121, 4397–4408
  • Sasabe , H. , Kihara , N. , Furusho , Y. , Mizuno , K. , Ogawa , A. and Takata , T. 2004 . Org. Lett. , 6 : 3957 – 3960 . (b) Aucagne, V.; Haenni, K.D.; Leigh, D.A.; Lusby, P.J.; Walker, D.B. J. Am. Chem. Soc. 2006, 128, 2186–2187. (c) Dichtel, W.R.; Miljanic, O.S.; Spruell, J.M.; Heath, J.R.; Stoddart, J.F. J. Am. Chem. Soc. 2006, 128, 10388–10390. (d) Hutin, M.; Schalley, C.A.; Bernardinelli, G.; Nitschke, J.R. Chem. Eur. J. 2006, 12, 4069–4076. (e) Mobian, P.; Collin, J.-P.; Sauvage, J.-P. Tetrahedron Lett. 2006, 47, 4907–4909. (f) Aucagne, V.; Berna, J.; Crowley, J.D.; Goldup, S.M.; Haenni, K.D.; Leigh, D.A.; Lusby, P.J.; Ronaldson, V.E.; Slawin, A.M.Z.; Viterisi, A.; Walker, D.B. J. Am. Chem. Soc. 2007, 129, 11950–11963. (g) Meyer, C.D.; Joiner, C.S.; Stoddart, J.F. Chem. Soc. Rev. 2007, 36, 1705–1723. (h) Durot, S.; Mobian, P.; Collin, J.-P.; Sauvage, J.-P. Tetrahedron 2008, 64, 8496–8503. (i) Prikhod'ko, A.I.; Durola, F.; Sauvage, J.-P. J. Am. Chem. Soc. 2008, 130, 448–449
  • Kolchinski , A.G. , Roesner , R.A. , Busch , D.H. and Alcock , N.W. 1998 . Chem. Commun. , : 1437 – 1438 . (b) Raymo, F.M.; Houk, K.N.; Stoddart, J.F. J. Am. Chem. Soc. 1998, 120, 9318–9322. (c) Cantrill, S.J.; Rowan, S.J.; Stoddart, J.F. Org. Lett. 1999, 1, 1363–1366. (d) Heim, C.; Affeld, A.; Nieger, M.; Vögtle, F. Helv. Chim. Acta 1999, 82, 746–759. (e) Rowan, S.J.; Stoddart, J.F. Org. Lett. 1999, 1, 1913–1916. (f) Baer, A.J.; Macartney, D.H. Inorg. Chem. 2000, 39, 1410–1417. (g) Chichak, K.; Walsh, M.C.; Branda, N.R. Chem. Commun. 2000, 847–848. (h) Furusho, Y.; Hasegawa, T.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 29, 18–19. (i) Chang, S.-Y.; Choi, J.; Jeong, K.-S. Chem. Eur. J. 2001, 7, 2687–2697. (j) Glink, P.T.; Oliva, A.I.; Stoddart, J.F.; White, A.J.P.; Williams, D.J. Angew. Chem. Int. Ed. 2001, 40, 1870–1875. (k) Gunter, M.J.; Bampos, N.; Johnstone, K.D.; Sanders, J.K.M. New J. Chem. 2001, 25, 166–173. (l) Hunter, C.A.; Low, C.M.R.; Packer, M.J.; Spey, S.E.; Vinter, J.G.; Vysotsky, M.O.; Zonta, C. Angew. Chem. Int. Ed. 2001, 40, 2678–2682
  • Balzani , V. , Venturi , M. and Credi , A. 2008 . Molecular Devices and Machines-Concepts and Perspectives for the Nanoworld , Weinheim : Wiley-VCH .
  • Cram , D.J. 1987 . Chem. Tech. , 17 : 120 – 125 . (b) Cram, D.J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009–1020
  • Cram , D.J. , Lein , G.M. , Kaneda , T. , Helgeson , R.C. , Knobler , C.B. , Maverick , E. and Trueblood , K.N. 1981 . J. Am. Chem. Soc. , 103 : 6228 – 6232 . (b) Cram, D.J.; Kaneda, T.; Helgeson, R.C.; Brown, S.B.; Knobler, C.B.; Maverick, E.; Trueblood, K.N. J. Am. Chem. Soc. 1985, 107, 3645–3657. (c) Reinhoudt, D.N.; Dijkstra, P.J.; In't Veld, P.J.A.; Bugge, K.E.; Harkema, S.; Ungaro, R.; Ghidini, E. J. Am. Chem. Soc. 1987, 109, 4761–4762. (d) Grootenhuis, P.D. J.; van Eerden, J.; Dijkstra, P.J.; Harkema, S.; Reinhoudt, D.N. J. Am. Chem. Sci. 1987, 109, 8044–8051. (e) Feinfoudt, D.N.; Dijkstra, P.J. Pure Appl. Chem. 1988, 60, 477–482. (f) Cram, D.J.; Carmack, R.A.; Helgeson, R.C. J. Am. Chem. Soc. 1988, 110, 571–577. (g) Auffinger, P.; Wipff, G. J. Am. Chem. Soc. 1991, 113, 5976–5988. (h) Ungaro, R.; Pochini, A. Front. Supramol. Org. Chem. Photochem. 1991, 57–81. (i) Carcanague, D.R.; Knobler, C.B.; Diederich, F.; J. Am. Chem. Soc. 1992, 114, 1515–1517. (j) Helgeson, R.C.; Selle, B.J.; Goldberg, I.; Knobler, C.B.; Cram, D.J. J. Am. Chem. Soc. 1993, 115, 11506–11511. (k) Judice, J.K.; Keipert, S.J.; Knobler, C.B.; Cram, D.J. J. Chem. Soc. Chem. Commun. 1993, 1325–1327. (l) Casnati, A.; Pochini, A.; Ungaro, R.; Ugozzoli, F.; Arnaud, F.; Fanni, S.; Schwing, M.-J.; Egberink, R.J.M.; de Jong, F.; Reinhoudt, D.N. J. Am. Chem. Soc. 1995, 117, 2767–2777. (m) Maverick, E.; Cram, D.J. Compr. Supramol. Chem. 1996, 1, 213–243. (n) Neri, P.; Consoli, G.M.L.; Cunsolo, F.; Geraci, C.; Piattelli, M. New J. Chem. 1996, 20, 433–446. (o) Yuan, Y.; Gao, G.; Jiang, Z.-L.; You, J.-S.; Zhou, Z.-Y.; Yuan, D.-Q.; Xie, R.-G. Tetrahedron 2002, 58, 8993–8999. (p) Rajakumar, P.; Srisailas, M. Tetrahedron Lett. 2003, 44, 2885–2887
  • Kim , H.-J. , Kim , H. , Alhakimi , G. , Jeong , E.J. , Thavarajah , N. , Studnicki , L. , Koprianiuk , A. , Lough , A.J. , Suh , J. and Chin , J. 2005 . J. Am. Chem. Soc. , 127 : 16370 – 16371 . (b) Ghalit, N.; Rijikers, D.T.S.; Kemmink, J.; Versluis, C.; Liskamp, R.M.J. Chem. Commun. 2005, 192–194. (c) Hou, H.; Leung, K.C.F.; Lanari, D.; Nelson, A.; Stoddart, J.F.; Grubbs, R.H. J. Am. Chem. Soc. 2006, 128, 15358–15359. (d) Murase, T.; Horiuchi, S.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 2866–2867
  • Grubbs , R.H. and Chang , S. 1998 . Tetrahedron , 54 : 4413 – 4450 . (b) Grubbs, R.H. Tetrahedron 2004, 60, 7117–7140. (c) Grubbs, R.H. Angew. Chem. Int. Ed. 2006, 45, 3760–3765. (d) Vougioukalakis, G.C.; Grubbs R.H. Chem. Rev. 2010, 110, 1746–1787
  • Wisner , J.A. , Beer , P.D. , Drew , M.G.B. and Sambrook , M.R. 2002 . J. Am. Chem. Soc. , 124 : 12469 – 12476 . (b) Coumans, R.G.E.; Elemans, J.A.A.W.; Thordarson, P.; Nolte, R.J.M.; Rowan, A.E. Angew. Chem. Int. Ed. 2003, 42, 650–654. (c) Hannam, J.S.; Kidd, T.J.; Leigh, D.A.; Wilson, A.J. Org. Lett. 2003, 5, 1907–1910. (d) Vignon, S.A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J.K.M.; Stoddart, J.F. J. Am. Chem. Soc. 2004, 126, 9884–9885
  • Mohr , B. , Weck , M. , Sauvage , J.-P. and Grubbs , R.H. 1997 . Angew. Chem. Int. Ed. Engl. , 36 : 1308 – 1310 . (b) Kidd, T.J.; Leigh, D.A.; Wilson, A.J. J. Am. Chem. Soc. 1999, 121, 1599–1600. (c) Weck, M.; Mohr, B.; Sauvage, J.-P.; Grubbs, R.H. J. Org. Chem. 1999, 64, 5463–5471. (d) Raehm, L.; Hamilton, D.G.; Sanders, J.K.M. Synlett 2002, 1743–1764. (e) Vysotsky, M.O.; Bolte, M.; Thondorf, I.; Boehmer, V. Chem. Eur. J. 2003, 9, 3375–3382. (f) Guidry, E.N.; Cantrill, S.J.; Stoddart, J.F.; Grubbs, R.H. Org. Lett. 2005, 7, 2129–2132
  • Iwamoto , H. , Itoh , K. , Nagamiya , H. and Fukazawa , Y. 2003 . Tetrahedron Lett. , 44 : 5773 – 5776 .
  • Iwamoto , H. , Yawata , Y. , Fukazawa , Y. and Haino , T. 2010 . Chem. Lett. , 39 : 24 – 25 .
  • Baeck , M. , Johansson , P.-O. , Waangsell , F. , Thorstensson , F. , Kvarnstroem , I. , Ayesa , S. , Waehling , H. , Pelcman , M. , Jansson , K. , Lindstroem , S. , Wallberg , H. , Classon , B. , Rydergaard , C. , Vrang , L. , Hamelink , E. , Hallberg , A. , Rosenquist , A. and Samuelsson , B. 2007 . Bioorg. Med. Chem. , 15 : 7184 – 7202 . (b) Hu, X.; Nguyen, K.T.; Jiang, V.C.; Lofland, D.; Moser, H.E.; Pei, D. J. Med. Chem. 2004, 47, 4941–4949. (c) Hattori, K.; Sajiki, H.; Hirota, K. Tetrahedron 2000, 56, 8433–8441
  • Yamaguchi , N. , Hamilton , L.M. and Gibson , H.W. 1998 . Angew. Chem. Int. Ed. , 37 : 3275 – 3279 .
  • Trnka , T.M. and Grubbs , R.H. 2001 . Acc. Chem. Res. , 34 : 18 – 29 .
  • Usui , S. , Haino , T. , Hayashibara , T. , Hirai , Y. , Fukazawa , Y. and Kodama , M. 1992 . Chem. Lett. , 21 : 527 – 530 . (b) Takahashi, T.; Yamada, H.; Haino, T.; Kido, Y.; Fukazawa, Y. Tetrahedron Lett. 1992, 33, 7561–7564
  • Mohamadi , F. , Richards , N.G.J. , Guida , W.C. , Liskamp , R. , Lipton , M. , Caufield , C. , Chang , G. , Hendrickson , T. and Still , W.C. 1990 . J. Comput. Chem. , 11 : 440 – 467 . (b) Reddy, M.R.; Erion, M.D.; Agarwal, A.; Viswanadhan, V.N.; McDonald, D.Q.; Still, W.C. J. Comput. Chem. 1998, 19, 769–780
  • Casadei , M.A. , Galli , C. and Mandolini , L.J. 1981 . J. Org. Chem. , 46 : 3127 – 3128 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.