Synlett 2013; 24(18): 2443-2445
DOI: 10.1055/s-0033-1339850
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Norbornahemicucurbiturils

Tomas Fiala
Department of Chemistry and Centre for Toxic Compounds in the Environment, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic   Fax: +420(549)492443   eMail: [email protected]
,
Vladimir Sindelar*
Department of Chemistry and Centre for Toxic Compounds in the Environment, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic   Fax: +420(549)492443   eMail: [email protected]
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Publikationsverlauf

Received: 25. Juli 2013

Accepted after revision: 27. August 2013

Publikationsdatum:
13. September 2013 (online)


Abstract

Ethyleneurea fused with a norbornane ring was prepared. Acid-catalyzed polycondensation of the urea with paraformaldehyde yielded a new six-membered hemicucurbituril derivative. The presence of hemicucurbiturils containing from four to eight monomer units were also detected.

Supporting Information

 
  • References and Notes

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  • 15 Norbornahemicucurbit[6]uril (NorHmCB[6]): Compound 1 (0.25 g, 1.6 mmol) was dissolved in 4 M aq HCl (20 mL) at 70 °C. Paraformaldehyde (0.054 g, 1.8 mmol of CH2O) was added and the resulting mixture was heated at 70 °C for 4 h (during this period a white precipitate formed). The solid material was collected by filtration, washed with H2O (10 mL), and dried in vacuo. The desired macrocyclic product was separated from the crude mixture by silica gel column chromatography (acetone–CHCl3, 1:4 v/v). Yield: 0.024 g (0.024 mmol, 8.9%); mp >250 °C. IR (KBr): 614 (m), 760 (m), 813 (w), 1216 (s), 1372 (s), 1441 (s), 1699 (s), 2871 (m), 2961 (m), 3437 (br m) cm–1. 1H NMR (300 MHz, CDCl3, 30 °C): δ = 1.28 (d, J = 13 Hz, 6 H, C(10)-HA), 1.34 (d, J = 11 Hz, 12 H, C(8,9)-HA), 1.40 (d, J = 11 Hz, 12 H, C(8,9)-HB), 1.57 (d, J = 13 Hz, 6 H, C(10)-HB), 2.63 (s, 12 H, C(1,7)-H), 3.50 (s, 12 H, C(2,6)-H), 4.59 (s, 12 H, C(11)-H2). 13C NMR (125 MHz, CDCl3, 30 °C): δ = 21.9 (C(8,9)-H2), 36.4 (C(10)-H2), 39.4 (C(1,7)-H), 49.1 (C(11)-H2), 57.0 (C(2,6)-H), 160.4 (C=O). HRMS: m/z calcd for [C54H72N12O6+H]+: 985.5771; found: 985.5777. Anal. Calcd for C54H72N12O6·2 H2O: C, 63.51; H, 7.50; N, 16.46. Found: C, 63.55; H, 7.55; N, 15.75.
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