Synthetic protocols towards homodithiacalix[n]arenes

Author:

Thomas Joice1,Dobrzańska Liliana1,Sonawane Mahendra Punjaji1,Smet Mario1,Maes Wouter2,Dehaen Wim1

Affiliation:

1. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

2. Design & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Universitaire Campus, Agoralaan 1 – Building D, 3590 Diepenbeek, Belgium

Publisher

Informa UK Limited

Subject

General Chemistry

Reference11 articles.

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2. Heteracalixarene reviews: (a) König, B.; Fonseca, M.H. Eur. J. Inorg. Chem.2000, 2000, 2303–2310; (b) Lhotak, P. Eur. J. Org. Chem.2004, 2004, 1675–1692; (c) Morohashi, N.; Narumi, F.; Iki, N.; Hattori, T.; Miyano, S. Chem. Rev.2006, 106, 5291–5316; (d) Kajiwara, T.; Iki, N.; Yamashita, M. Coord. Chem. Rev.2007, 251, 1734–1746; (e) Tsue, H.; Ishibashi, K.; Tamura, R. Top. Heterocycl. Chem.2008, 17, 73–96; (f) Maes, W.; Dehaen, W. Chem. Soc. Rev.2008, 37, 2393–2402; (g) Wang, M.X. Chem. Commun.2008, 4541–4551; (h) Wang, M.X. Acc. Chem. Res. 2012, 45, 182–192.

3. Homoazacalixarenes: (a) Takemura, H. J. Inclusion Phenom. Macrocyclic. Chem.2002, 42, 169–186; (b) Ito, K.; Noike, M.; Kida, A.; Ohba, Y. J. Org. Chem.2002, 67, 7519–7522; (c) Kaewtong, C.; Fuangswasdi, S.; Muangsin, N.; Chaichit, N.; Vicens, J.; Pulpoka, B. Org. Lett.2006, 8, 1561–1564; (d) Khan, S.; Singh, J.D.; Mahajan, R.K.; Sood, P. Tetrahedron Lett.2007, 48, 3605–3608; (e) Kaewtong, C.; Jiang, G.; Park, Y.; Fulghum, T.; Baba, A.; Pulpoka, B.; Advincula, R. Chem. Mater.2008, 20, 4915–4924; (f) Arunachalam, M.; Ravikumar, I.; Ghosh, P. J. Org. Chem.2008, 73, 9144–9147; (g) Takemura, H.; Yonebayashi, Y.; Nakagaki, T.; Shinmyozu, T. Eur. J. Org. Chem.2011, 2011, 1968–1971.

4. Homooxacalixarenes: (a) Masci, B.; Finelli, M.; Varrone, M. Chem.Eur. J.1998, 4, 2018–2030; (b) Shokova, E.A.; Kovalev, V.V. Russ. J. Org. Chem.2004, 40, 607–643; (c) Shokova, E.A.; Kovalev, V.V. Russ. J. Org. Chem.2004, 40, 1547–1571; (d) Masci, B.; Mortera, S.L.; Persiani, D.; Thuéry, P. J. Org. Chem.2006, 71, 504–511; (e) Choi, J.K.; Lee, A.; Kim, S.; Ham, S.; No, K.; Kim, J.S. Org. Lett.2006, 8, 1601–1604; (f) Kohmoto, S.; Someya, Y.; Masu, H.; Yamaguchi, K.; Kishikawa, K.J. Org. Chem.2006, 71, 4509–4515; (g) Notestein, J.M.; Andrini, L.R.; Kalchenko, V.I.; Requejo, F.G.; Katz, A.; Iglesia, E. J. Am. Chem. Soc.2007, 129, 1122–1131; (h) Redshaw, C.; Rowan, M.A.; Warford, L.; Homden, D.M.; Arbaoui, A.; Elsegood, M.R.J.; Dale, S.H.; Yamato, T.; Casas, C.P.; Matsui, S.; Matsuura, S. Chem.Eur. J.2007, 13, 1090–1107; (i) Marcos, P.M.; Ascenso, J.R.; Segurado, M. A.P.; Bernardino, R.J.; Cragg, P.J. Tetrahedron2009, 65, 496–503; (j) Ni, X.L.; Wang, S.; Zeng, X.; Tao, Z.; Yamato, T. Org. Lett.2011, 13, 552–555; (k) Cottet, K.; Marcos, P.M.; Cragg, P.J. Beilstein J. Org. Chem.2012, 8, 201–226.

5. Homothiacalixarenes: (a) Mitchell, R.H.; Boekelheide, V.J. Am. Chem. Soc. 1974, 96, 1547–1557; (b) Tashiro, M.; Yamato, T. J. Org. Chem.1981, 46, 1543–1552; (c) Takido, T.; Toriyama, M.; Ogura, K.; Kamijo, H.; Motohashi, S.; Seno, M. Phosphorus Sulfur Silicon Relat. Elem.2003, 178, 1295–1301; (d) Kohno, K.; Takeshita, M.; Yamato, T. J. Chem. Res.2006, 2006, 251–253; (e) Ashram, M. J. Inclusion Phenom. Macrocyclic Chem.2006, 54, 253–259; (f) Tran, H.A.; Georghiou, P.E. New J. Chem.2007, 31, 921–926; (g) Thomas, J.; Van Hecke, K.; Robeyns, K.; Van Rossom, W.; Sonawane, M.P.; Van Meervelt, L.; Smet, M.; Maes, W.; Dehaen, W. Chem. Eur. J.2011, 17, 10339–10349; (h) Sonawane, M.; Jacobs, J.; Van Hecke, K.; Thomas, J.; Van Meervelt, L.; Dehaen, W.; Van Rossom, W. J. Org. Chem.2012, 77, 8444–8450.

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