Efficient synthesis of water-soluble calixarenes using click chemistry

Organic Letters

Volumn 7, Issue 6, 2005, Pages 1035-1037

  Ryu, Eui Hyun ^a   Zhao, Yan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS;

CALIXARENES; CHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SOLUBILITY; WATER;

EID: 18244371903     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047468h     Document Type: Article

References (41)

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35. Large difference in the solubility of 2 and azidoacetic acid was probably responsible for the poor results. High temperature might have promoted the side reaction, homocoupling of alkynes; see: (a) Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. D., Ed.; Marcel Dekker: New York, 1969; pp 597-648. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064. (c) Ref 15.
36. Large difference in the solubility of 2 and azidoacetic acid was probably responsible for the poor results. High temperature might have promoted the side reaction, homocoupling of alkynes; see: (a) Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. D., Ed.; Marcel Dekker: New York, 1969; pp 597-648. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064. (c) Ref 15.
37. Large difference in the solubility of 2 and azidoacetic acid was probably responsible for the poor results. High temperature might have promoted the side reaction, homocoupling of alkynes; see: (a) Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. D., Ed.; Marcel Dekker: New York, 1969; pp 597-648. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064. (c) Ref 15.
38. Alkyne 5a was prepared by ring opening of δ-gluconolactone with propargylamine in 97% yield. Alkynes 5b and 5c were prepared in 92 and 80% yields by nucleophilic substitution of propargyl bromide by sodium sulfite and trimethylamine, respectively. See Supporting Information for experimental details.
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40. -5 M in water, see: Sgura, M.; Sansone, F.; Casnati, A.; Ungaro, R. Synthesis 2001, 2105-2112.
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