Rotaxanes via Michael addition

Organic Letters

Volumn 2, Issue 5, 2000, Pages 593-595

  Reuter, Carin ^a   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001631546     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990350u     Document Type: Article

References (39)

1. (a) Rotaxanes are molecules that consist of one or more wheels and penetrating axles; these are mechanically bound together and sterically prevented from dethreading by bulky stopper groups at both ends of the axles. Harrison, I. T.; Harrison, S. J. Am. Chem. Soc. 1967, 89, 5723-5724.
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19. Because of the low acidity of common CH acids, it was not possible to use carbon nucleophiles; the strong bases needed for their deprotonation also led to a deprotonation of the carbonamide groups of wheel 4.
20. For complexes such as [1-4] the term supramolecular nucleophiles was coined, see ref 4a. The molecular recognition of the anionic stoppers results from hydrogen bonding with one of the two isophthalamide units of the wheel 4, whose hydrogens are pointing toward the cycle's center, as shown by X-ray structure analyses: (a) Fischer, C.; Nieger, M.; Mogck, O.; Böhmer, V.; Ungaro, R.; Vögtle, F. Eur. J. Org. Chem. 1998, 155-161.
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37. This is similar to the (Z)-addition of thioisocyanate to N-methyl-propiolamide: Crow, W. D.; Leonard, N. J. J. Org. Chem. 1965, 30, 2660-2665.
38. 8a, see ref 4b; 8b, see Supporting Information.
39. Parham, A. H.; Windisch, B.; Vögtle, F. Eur. J. Org. Chem. 1999, 1233-1238.