Template synthesis of [2]rotaxanes with large ring components and tris(biphenyl)methyl group as the blocking group. The relationship between the ring size and the stability of the rotaxanes

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7477-7480

  Saito, Shinichi ^a   Nakazono, Kazuko ^a   Takahashi, Eiko ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

RINGS (COMPONENTS); SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

BLOCKING GROUP; ROTAXANES; TEMPLATE METHOD; TRISBIPHENYLMETHYL;

AROMATIC COMPOUNDS;

BIPHENYL DERIVATIVE; METHYL GROUP; ROTAXANE;

ARTICLE; CHEMICAL REACTION KINETICS; CONFORMATION; MOLECULAR SIZE; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 33748998172     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060829h     Document Type: Article

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44. Though we confirmed the formation of 9 by the NMR analysis of the crude mixture, we could not isolate 9 in pure form. See Supporting Information for the NMR spectra of 9a.
45. The formation of 11 might occur if the conformation of 9 was not suitable for the formation of the rotaxane when the C-O bond forming reaction proceeded. Incomplete formation of 9 might also result in the formation of 11.
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47. See Supporting Information.
48. 1/2 for the reaction of 10b at 27 °C was ca. 200 h. Considering the time required for the decomplexation and purification, we assume that the partial dissociation took place. In solid state, 10b could be stored in a freezer (-20 °C) for a couple of months without dissociation.