Synthesis of a novel 1,4-bridged calix[8]arene 'host' cavity

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5411-5414

  Tsantrizos, Youla S ^a   Chew, Warren ^a   Colebrook, Lawrence D ^a   Sauriol, Françoise ^b  

^a Gina Cody School of Engineering and Computer Science   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

ARENE;

EID: 0030755728     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01202-1     Document Type: Article

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25. +.
26. 3), 4.62 (m) and 5.66 (br d) (C3′-CHaHb-O-C), 6.86 (H4′) and 7.26 (H6′). calix[8]arene moiety: (a) A rings δ 1.15 (s, t-Bu), 7.02 (d, J = 1.8 Hz, Ha), 6.91 (d, J = 1.8 Hz, Hb), 4.18 and 3.46 (2d, J = 13.9 Hz, A-CHaHb-A). 4.02 and 3.51 (2d, J =15.4 Hz , A-CHaHb-B); (b) B rings δ 1.27 (s, t-Bu), 7.06 (d, J = 2.2 Hz, Ha), 7.15 (d, J = 2.2 Hz, Hb), 4.40 and 3.72 (2d, J = 14.4 Hz, B-CHaHb-C); (c) C rings δ 1.22 (s, t-Bu), 7.09 (d, J = 2.0 Hz, Ha), 7.13 (d, J = 2.0 Hz, Hb), 3.35 and 3.98 (2d, J = 14.8 Hz, C-CHaHb-D); (d) D rings δ 0.98 (s, t-Bu), 6.43 (very broad, Ha), 6.93 (broad, Hb), 4.85 and 4.28 (2d, J = 18.3 Hz, D-CHaHb-D); OH groups 7.65, 8.18, 8.19 all very broad.
27. Although the relative minimized energies for the 1,3- and 1,5-bridged analogs were within 1-2 kcal/mol of that of the 1,4-bridged analog, the NMR data were not consistent with either a 1,3- or a 1,5-bridged structure.