A novel synthesis of 2'-hydroxy-1',3'-xylyl crown ethers

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Leij, M. van der and Oosterink, H.J. and Hall, R.H. and Reinhoudt, D.N. (1981) A novel synthesis of 2'-hydroxy-1',3'-xylyl crown ethers. Tetrahedron, 37 (21). pp. 3661-3666. ISSN 0040-4020

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Abstract:Six novel 2' - hydroxy - 1',3' - xylyl crown ethers (8a–e and 13)1 have been synthesized utilizing the allyl group to protect the OH function during the cyclization reaction. The macrocycles 6a-e were formed in yields of 26 to 52%, by intermolecular reaction of 4 - chloro - 2,6 - bis(bromomethyl) - 1 - (2 - propenyloxy)benzene (5) with polyethylene glycols; 6a was also obtained by an intramolecular cyclization reaction of monotosylate 14.
A 30-membered ring with a 2' - hydroxy - 1',3' - xylyl sub-unit was obtained in 87% yield by reaction of ditosylate 9 with bis [2 - (o - hydroxyphenoxy)ethyl]ether (11) in the presence of cesium fluoride. The synthesis of crown ethers with a 2' - hydroxy - 1',3' - xylyl sub-unit (1c–e, H for CH3) by demethylation of the corresponding 2'-methoxy crown ethers 1c–e with lithium iodide were unsuccessful; it would appear that the demethylation reaction is restricted to 15- and 18-membered rings. One of the 2' - hydroxy - 1',3' - xylyl crown ethers 8d forms a crystalline 1:1-complex with water.
Item Type:Article
Copyright:© 1981 Elsevier Science
Link to this item:http://purl.utwente.nl/publications/68756
Official URL:http://dx.doi.org/10.1016/S0040-4020(01)98895-7
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