The Synthesis of Axially Chiral Resorcinarenes from Resorcinol Monoalkyl Ethers and Aldehyde Dimethylacetals

Jonathan Y. Boxhall; Philip C. Bulman Page; Mark R. J. Elsegood; Yohan Chan; Harry Heaney; Kathryn E. Holmes; Matthew J. McGrath

doi:10.1055/s-2003-39294

LETTER

The Synthesis of Axially Chiral Resorcinarenes from Resorcinol Monoalkyl Ethers and Aldehyde Dimethylacetals

Jonathan Y. Boxhall, Philip C. Bulman Page, Mark R. J. Elsegood, Yohan Chan, Harry Heaney*, Kathryn E. Holmes, Matthew J. McGrath
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK
Fax: +44(1509)223925; e-Mail: h.heaney@lboro.ac.uk;

Abstract

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Abstract

Novel racemic tetraalkoxyresorcinarene derivatives can be prepared in good yields by boron trifluoride diethyl etherate-catalysed reactions of 1,1-dimethoxyalkanes with resorcinol monoalkyl ethers.

Key words

dimethylacetals - boron trifluoride - calixarenes - resorcinarenes - resorcinol monoalkyl ethers

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Referenzen

References

1a Gutsche CD. Calixarenes Revisited The Royal Society of Chemistry; Cambridge, England: 1998.

1b Calixarenes in Action Mandolini L. Ungaro R. Imperial College Press; London: 2000.

1c Calixarenes 2001 Asfari Z. Böhmer V. Harrofield J. Vicens J. Kluwer; Dordrecht: 2001.

2a Botta B. Delle Monache G. De Rosa MC. Carbonetti A. Gacs-Baitz E. Botta M. Corelli F. Misiti D. J. Org. Chem. 1995, 60: 3657

2b Iwanek W. Tetrahedron Lett. 1998, 54: 14089

2c Iwanek W. Syzdól B. Synth. Commun. 1999, 29: 1209

2d Konishi H. Sakakibara H. Kobayashi K. Morikawa O. J. Chem. Soc., Perkin Trans. 1 1999, 2583

3 McIldowie MJ. Mocerino M. Skelton BW. White AH. Org. Lett. 2000, 2: 3869

4

The abbreviated structures, shown as a tetramer in Scheme [1] , Scheme [2] , Scheme [3] and Scheme [5] , are taken to represent a cyclic structure viewed from the inside of the resorcinarene and with the pendent alkyl chains in pseudoaxial orientations.

5a Iwanek W. Mattay J. Liebigs Ann. Chem. 1995, 1463

5b El Gihani MT. Heaney H. Slawin AMZ. Tetrahedron Lett. 1995, 36: 4905

5c Arnecke R. Böhmer V. Friebe S. Gebauer S. Krauss GJ. Thondorf I. Vogt W. Tetrahedron Lett. 1995, 36: 6221

6 Page PCB. Heaney H. Sampler EP. J. Am. Chem. Soc. 1999, 121: 6751

7 Boxhall JY. Page PCB. Chan Y. Hayman CM. Heaney H. McGrath MJ. Synlett 2003, 997

8

Tetra-iso-propyloxyresorcinarene(1). MS (FAB): m/z [M + H⁺] found 937.65710. C₆₀H₈₉O₈ requires 937.65579. Found: C, 76.91; H, 9.41%. C₆₀H₈₈O₈ requires C, 76.88, H, 9.46%. IR: ν_max = 3418, 2931, 2089, 1626, 1494, 1108, 738 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 0.89 (t, 12 H, J = 7.2 Hz), 1.26-1.40 (m, 48 H), 2.14-2.23 (m, 8 H), 4.27 (t, 4 H, J = 7.6 Hz), 4.55 (sept., 4 H, J = 6.4 Hz), 6.34 (s, 4 H), 7.23 (s, 4 H), 7.69 (s, 4 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ_C = 14.15 (Me), 21.85 (Me), 21.87 (Me), 22.72 (CH₂), 27.81 (CH₂), 31.96 (CH₂), 33.40 (CH), 34.05 (CH₂), 71.81 (CH), 102.61 (CH), 123.77 (CH), 125.43 (C), 125.67 (C), 151.77 (C), 152.88 (C) ppm.

9a Crombie L. Josephs JL. J. Chem. Soc., Perkin Trans. 1 1993, 2591

9b Mendelson WL. Holmes M. Dougherty J. Synth. Commun. 1996, 26: 593

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Crystallographic data in cif format (ref. CCDC 206434 & 206435). Copies can be obtained free of charge from: CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK, or e-mail: deposit@ccdc.cam.ac.uk or www.ccdc.cam.ac.uk.

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MS (FAB): m/z (100%) [M + H⁺] found 1041.71790, C₆₈H₉₂O₈ requires 1041.71830. ¹H NMR (400 MHz, CDCl₃): δ = 0.89 (m, 12 H), 1.30 (m, 24 H), 1.75 (m, 32 H), 2.17 (m, 8 H), 4.24 (t, 4 H, J = 7.8 Hz), 6.36 (s, 4 H), 7.23 (s, 4 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ =14.55 (Me), 23.08 (CH₂), 24.07 (CH₂), 24.41 (CH₂), 28.11 (CH₂), 32.23 (CH₂), 33.29 (CH₂), 33.59 (CH), 34.34 (CH₂), 81.50 (CH), 102.91 (CH), 124.03 (CH), 125.50 (C), 125.79 (C), 152.06 (C), 152.99 (C) ppm.