Subscribe to RSS
DOI: 10.1055/s-2003-36803
Synthesis and Characterization of Chiral Calixarene Analogs Locked in the Cone Conformation by the Photocycloaddition
Publication History
Publication Date:
22 January 2003 (online)
Abstract
A bisphenol derivative was used as the starting material. [2+2] Photocycloaddition of tetraolefin gave the desired calix[4]arene analogs having chiral and achiral structure in 12-77% yields. The optical resolution was successfully achieved by using the HPLC method. The calixarene analog formed a 1:1 complex with alkali metal ions and extracted large metal picrates better than small ones.
Key words
calixarene - cyclophane - photocycloaddition - alkali metal
- 1
Okada Y.Sugiyama K.Wada Y.Nishimura J. Tetrahedron Lett. 1990, 31: 107 - 2
Okada Y.Ishii F.Kasai Y.Nishimura J. Chem. Lett. 1992, 755 - 3
Okada Y.Mabuchi S.Kurahayashi M.Nishimura J. Chem. Lett. 1991, 1345 - 4
Okada Y.Hagihara M.Mineo M.Nishimura J. Synlett 1998, 269 - 5
Calixarenes
50th Anniversary
Vicens J.Asfari Z.Harrowfield JM. Kluwer; Dordrecht: 1994. - 6
Böhmer V. Angew. Chem. Int. Ed. Engl. 1995, 34: 713 - 7
Okada Y.Ishii F.Kasai Y.Nishimura J. Tetrahedron Lett. 1993, 34: 1971 - 8
Okada Y.Kasai Y.Nishimura J. Tetrahedron Lett. 1995, 36: 555 - 9
Okada Y.Mizutani M.Ishii F.Nishimura J. Tetrahedron Lett. 1997, 38: 9013 - 10
Kimura M.Shimoyama M.Morosawa S. J. Chem. Soc. Chem. Commun. 1991, 375 - 12
Okada Y.Mizutani M.Ishii F.Kasai Y.Nishimura J. Tetrahedron 2001, 57: 1219 - 13
Okada Y.Mizutani M.Ishii F.Nishimura J. Synlett 2000, 41 - 14
Okada Y.Mizutani M.Ishii F.Nishimura J. Tetrahedron Lett. 1999, 40: 1353 - 15
Okada Y.Mizutani M.Nishimura J. Tetrahedron Lett. 1998, 39: 8467 - 16
Okada Y.Mizutani M.Ishii F.Nishimura J. Tetrahedron Lett. 1998, 39: 8461
References
Compd.: MS (M+): 1H NMR δ (intensity, multiplicity, J in Hz). 5c: Calcd for C42H46O6: 646: 2.16-2.62 (8 H, m), 3.17 (2 H, d, 15), 3.52 (2 H, m), 3.58-3.70 (6 H, m), 3.75 (6 H, s), 3.77-3.83 (4 H, m), 4.13 (2 H, m), 4.22 (2 H, d, 15), 4.43 (2 H, m), 5.94 (2 H, dd, 1.8, 8.0), 6.17 (2 H, dd, 1.8, 8.0), 6.32 (2 H, t, 8.0), 7.07 (2 H, dd, 1.8, 8.0), 7.16 (2 H, t, 8.0), 7.38 (2 H, dd, 1.8, 8.0). 6c: Calcd for C42H46O6: 646: 2.24-2.58 (8 H, m), 3.17 (2 H, d, 15), 3.26 (6 H, s), 3.50-3.95 (12 H, m), 4.21 (2 H, d, 15), 4.16 (2 H, m), 4.60 (2 H, m), 6.44 (2 H, dd, 2.0, 7.8), 6.67 (2 H, dd, 2.0, 7.8), 6.69 (2 H, t, 7.8), 6.76 (2 H, dd, 2.0, 7.8), 6.81 (2 H, t, 7.8), 6.86 (2 H, dd, 2.0, 7.8). 5d: Calcd for C44H50O7: 690: 2.24-2.52 (8 H, m), 3.13 (2 H, d, 15), 3.63 (6 H, s), 3.64-4.06 (16 H, m), 4.16 (2 H, d, 15), 4.26 (2 H, m), 4.36 (2 H, m), 6.40 (2 H, dd, 1.8, 7.5), 6.56 (2 H, dd, 1.8, 7.5), 6.63 (2 H, t, 7.5), 6.67 (2 H, dd, 1.8 & 7.5), 6.86 (2 H, t, 7.5), 6.98 (2 H, dd, 1.8, 7.5). 6d: Calcd for C44H50O7: 690: 2.26-2.50 (8 H, m), 3.17 (2 H, d, 15), 3.20 (6 H, s), 3.58-3.94 (16 H, m), 4.26 (2 H, d, 15), 4.28 (2 H, m), 4.44 (2 H, m), 6.52 (2 H, dd, 1.8, 7.5), 6.66 (2 H, dd, 1.8, 7.5), 6.72 (2 H, dd, 1.8, 7.8), 6.76 (2 H, t, 7.5), 6.78 (2 H, dd, 1.8, 7.5), 6.83 (2 H, dd, 1.8, 7.5).