A Novel Synthesis of 2'-Hydroxy-1',3'-Xylyl Crown Ethers
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. © 1981.
Recommended Citation
van der Leij, M., Oosterink, H. J., Hall, R. H., & Reinhoudt, D. N. (1981). A Novel Synthesis of 2'-Hydroxy-1',3'-Xylyl Crown Ethers. Tetrahedron, 37(21), pp. 3661-3666. Elsevier.
The definitive version is available at https://doi.org/10.1016/S0040-4020(01)98895-7
Department(s)
Business and Information Technology
International Standard Serial Number (ISSN)
0040-4020
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 Elsevier, All rights reserved.
Publication Date
01 Jan 1981
