Facile Transformation of the Hydroxy‐Substituted Oxathiacrown Ethers

Abstract

9(12)‐Hydroxy‐dithia‐13(16)‐crown‐4(6)‐ethers have been prepared by the condensing an oligoethylene glycol dithiol with 2,3‐dibromo‐1‐propanol. Methods of oxidation, halogenation, amination, and esterification of the 9‐hydroxythiacrown ether, producing corresponding oxathiacrown ether derivatives in good yields, have been developed. Cyclic destruction has not been found in the studied reactions. The change of the oxathiamacrocyclic ring size in the course of the halogenation and amination reactions was revealed.

Keywords:

• Crown ether
• 2,3‐dibromo‐1‐propanol
• esterification
• halogenation
• oligoethylene glycol dithiol
• oxidation

Acknowledgment

This work was supported by the INTAS (Grant 03‐51‐4696), Russian Fund of Basic Research (Grant 05‐03‐33201).