Mild and high-yielding syntheses of diethyl phosphoramidate-stoppered [2]rotaxanes

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4183-4186

  Hung, Wei Chung ^a   Liao, Kang Shyang ^a   Liu, Yi Hung ^a   Peng, Shie Ming ^a   Chiu, Sheng Hsien ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; CROWN ETHER DERIVATIVE; ROTAXANE;

ARTICLE; MOLECULAR RECOGNITION; QUANTITATIVE ANALYSIS; SOLID; SYNTHESIS;

EID: 9444285528     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0484557     Document Type: Article

References (49)

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33. -1) for the binding of DPT24C8 with a more soluble and more strongly binding salt, bis(4-fluorobenzyl)ammonium hexafluorophosphate. See: Ashton, P. R.; Fyfe, M. C. T.; Hickingbottom, S. K.; Stoddart, J. F.; White, A. J. P.; Williams D. J. J. Chem. Soc., Perkin Trans. 2 1998, 2117-2124 and ref 11.
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41. a determined in this way are merely "ballpark" figures (see Supporting Information); for a discussion of a method for determining the values more precisely, see: Jones, W. J.; Gibson, H. W. J. Am. Chem. Soc. 2003, 125, 7001-7004.
42. a determined in this way are merely "ballpark" figures (see Supporting Information); for a discussion of a method for determining the values more precisely, see: Jones, W. J.; Gibson, H. W. J. Am. Chem. Soc. 2003, 125, 7001-7004.
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45. In related pseudorotaxane systems, the use of DMSO as a solvent disrupts hydrogen bonding to such an extent that no complex forms; thus, dissolving a rotaxane of this type in DMSO is a good test for the degree of interlocking of the components. For example, see: Chiu, S.-H.; Rowan, S. J.; Cantrill, S. J.; Glink, P. T.; Garrell, R. L.; Stoddart, J. F. Org. Lett. 2000, 2, 3631-3634.
46. The p-tert-butylbenzyl group is a true stopper for DB24C8 rings, but the p-isopropylbenzyl group is a slippage stopper; see: Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297-2307. The diethyl phosphoramidate group is larger sterically than an isopropyl group when inspected using CPK molecular models.
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48. -1).
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