Desilylation-triggered isomerization of a molecular capsule from an open-type to a collapsed-type isomer

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3569-3572

  Watanabe, Soichiro ^a,c   Goto, Kei ^a,d   Kawashima, Takayuki ^a   Okazaki, Renji ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN WOMEN'S UNIVERSITY   (Japan)

^c TOHO UNIVERSITY   (Japan)

^d KITASATO UNIVERSITY   (Japan)

Author keywords

Carcerands; Deblocking; Isomerization; Kinetics

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CONFORMATIONAL TRANSITION; ISOMERISM; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0033617458     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00574-2     Document Type: Article

References (9)

1. [1] Cram DJ, Cram JM. Container molecules and their guests. Cambridge: The Royal Society of Chemistry, 1994.
2. [2] For a review of switchable receptor molecules, see: Shinkai S. In: Gokel GW, editor. Comprehensive Supramolecular Chemistry, Vol. 1. Oxford: Elsevier, 1996: 671-700.
3. [3] Watanabe S, Goto K, Kawashima T, Okazaki R. Tetrahedron Lett. 1995;36:7677-7680.
4. [4] For related compounds, see: Watanabe S, Goto K, Kawashima T, Okazaki R. J. Am. Chem. Soc. 1997;119:3195-3196.
5. 3) δ 14.04 (q), 14.05 (q), 22.64 (t), 27.86 (t), 27.91 (t), 29.38 (t), 29.50 (t), 29.52 (t), 29.92 (t), 31.83 (t), 31.89 (t), 36.83 (d), 36.92 (d), 68.55 (t), 72.01 (t), 98.51 (t), 98.75 (t), 108.89 (d), 114.40 (d), 116.08 (d), 117.25 (d), 125.15 (d), 126.88 (d), 128.43 (d), 128.82 (d), 129.20 (d), 130.56 (d), 136.37 (s), 138.55 (s), 139.07 (s), 139.23 (s), 139.37 (s), 140.28 (s), 143.47 (s), 148.15 (s), 148.21 (s), 159.83 (s).
6. [6] Hart et al. reported the similar thermal isomerization of the cappdophane from the thermodynamically unfavorable isomer to the favored one. Vinod TK, Hart H. J. Org. Chem. 1991;56:5630-5640.
7. [7] Mohamadi F, Richards NGJ, Guida WC, Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still WC. J. Comput. Chem. 1990;11:440-467.
8. [8] Halgren TA. J. Comput. Chem. 1996;17:490, 520, 553, 587, 616.
9. [9] Hall M., Harris MM. J. Chem. Soc. 1960;490-494.