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

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

References

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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.

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.

10

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: [e-mail] or www.ccdc.cam.ac.uk.

11

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.