Bulletin of the Chemical Society of Japan p. 1689 - 1693 (1980)
Update date:2022-08-28
Topics:
Kuo, Ping-Lin
Kawamura, Norio
Miki, Masaki
Okahara, Mitsuo
A new facile method of synthesizing crown ethers from oligoethylene glycols by treating them with arenesulfonyl or alkanesulfonyl chlorides in the presence of alkali metal hydroxide or alkoxide was described. 15-Crown-5 and 21-crown-7 were synthesized from pentaethylene glycol and heptaethylene glycol respectively in good yields, while 18-crown-6 was obtained from both hexaethylene glycol and triethylene glycol.Although the main product was 24-crown-8 in the reaction of tetraethylene glycol/TsCl/Na(K)OH in dioxane, 12-crown-4 was obtained in a moderate yield from the reaction of tetraethylene glycol/benzenesulfonyl chloride/t-BuOLi in t-BuOH.Furthermore, the analogous treatment of PEG 200 afforded a mixture of 15-, 18-, 21- and 24-crown ethers.The reaction conditions were investigated, and the scope of the reaction was discussed.
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