Anion helicates: Double strand helical self-assembly of chiral bicyclic guanidinium dimers and tetramers around sulfate templates

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 277-278

  Sánchez Quesada, Jorge ^a   Seel, Christian ^a   Prados, Pilar ^a   De Mendoza, Javier ^a   Dalcol, Ionara ^b   Giralt, Ernest ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038911680     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953243d     Document Type: Article

References (30)

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2. Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1-76. For a recent example of helicenes, see: Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 50, 6787-6795 and references therein.
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26. Peschke, W.; Schiessl, P.; Schmidtchen. F. P.; Bissinger. P.; Schier, A. J. Org. Chem. 1995, 60, 1039-1043. Improved procedures for the syntheses of 2 and 4 were employed. No disulfide formation was detected in the preparation of 2 with sodium sulfide. On the other hand, the yield of pure 4 as a colorless solid was enhanced from 59% to 84% by reaction of the corresponding guanidinium alcohol (Kato, Y.; Conn, M. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1994, 116, 3279-3284) with carbon tetrabromide and tetraphenylphosphine instead of thionyl bromide.
27. Peschke, W.; Schiessl, P.; Schmidtchen. F. P.; Bissinger. P.; Schier, A. J. Org. Chem. 1995, 60, 1039-1043. Improved procedures for the syntheses of 2 and 4 were employed. No disulfide formation was detected in the preparation of 2 with sodium sulfide. On the other hand, the yield of pure 4 as a colorless solid was enhanced from 59% to 84% by reaction of the corresponding guanidinium alcohol (Kato, Y.; Conn, M. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1994, 116, 3279-3284) with carbon tetrabromide and tetraphenylphosphine instead of thionyl bromide.
28. Unless specified, counterions refer to chloride. The synthetic scheme was performed either with guanidines of (R,R) or (S,S) configuration, although only compounds with (R) configuration are shown in the formulae. All new compounds were characterized by a full complement of high-resolution spectra and elemental microanalyses for C and H which are within 0.40% theory.
29. 3 (10 mg/mL). The additional cross peaks present in the ROESY spectra of (R,R)-3 sulfate, compared to the ROESY spectra of the dichioride. do not disappear on dilution of the sample, excluding the possibility of these being due to molecular contacts
30. 1f- with Insight-II 2.3.0/Discover packages (Biosym) using AMBER force field. CHARMM parameters and Spartan 3.0 electrostatic charges at the 6-31G* level were used for sulfate.