Synthesis and assembly of self-complementary cavitands

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4573-4582

  Renslo, Adam R ^a   Tucci, Fabio C ^a   Rudkevich, Dmitry M ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE;

ARTICLE; CONFORMATION; COVALENT BOND; DIMERIZATION; ENTHALPY; ENTROPY; HYDROGEN BOND; SYNTHESIS; THERMOSTABILITY;

EID: 0034679113     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993922e     Document Type: Article

References (47)

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31. Selective tri-arylation of a resorcinarene with quinoxaline dichlorides was reported previously, see: (a) Soncini, P.; Bonsignore, S.; Dalcanale, E.; Ugozzoli, F. J. Org. Chem. 1992, 57, 4608-4612. (b) Reference 10a.
32. Selective tri-arylation of a resorcinarene with quinoxaline dichlorides was reported previously, see: (a) Soncini, P.; Bonsignore, S.; Dalcanale, E.; Ugozzoli, F. J. Org. Chem. 1992, 57, 4608-4612. (b) Reference 10a.
33. A single regioisomer is formed. We presume that nucleophilic attack occurs at the more electrophilic position on quinoxaline dichlorides to give the regioisomer shown (i.e., SCCs 4).
34. 15 amide groups around the upper rim of the structure).
35. 8 solvent was used with 5.
36. This is supported by the observation of chemical exchange cross-peaks between adamantane signals in the ROESY spectrum of 4b·4b.
37. The surprisingly large effect of this change suggests that the amide plays a crucial role in stabilizing the dimeric structure, probably as a hydrogen bond donor/acceptor. The substitution of amide for ester is destabilizing to a greater extent than simple loss of a hydrogen bond donor and so it seems likely that lone pair-lone pair repulsion is additionally destabilizing in the case of 4c.
38. The source of the increased binding enthalpy and entropy in 3b (as compared to 3a) is not readily apparent. Without detailed (crystallographic) information regarding the structure of these dimers, this issue cannot be meaningfully addressed.
39. 10 solvent.
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47. This synthetic approach was employed in the synthesis of deepened cavitands: Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Org. Chem. 1999, 64, 4555-4559.