DOI: 10.1246/bcsj.55.2005. Synthesis and Alkali-cation Complexing Properties of 12-Crown-4 Derivatives

Synthesis and Alkali-cation Complexing Properties of 12-Crown-4 Derivatives

10.1246/bcsj.55.2005

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Benzyloxymethyl-12-crown-4, a precursor of hydroxymethyl-12-crown-4, is prepared in an excellent yield by the reaction of 3-benzyloxy-1,2-propanediol with 1,8-dichloro-3,6-dioxaoctane in the heterogeneous t-BuOLi/t-BuOH/LiBr·2H2O reaction system. The hydrogenolysis in the presence of p-toluenesulfonic acid leads to a good yield of hydroxymethyl-12-crown-4. The sandwich-type 2:1 complexation with Na+ of 12-crown-4 and hydroxymethyl-12-crown-4 derivatives was discussed on the basis of the stability constants and the solvent extraction in the CH2Cl2–water system.

Bibliography

Miyazaki, T., Yanagida, S., Itoh, A., & Okahara, M. (1982). Synthesis and Alkali-cation Complexing Properties of 12-Crown-4 Derivatives. Bulletin of the Chemical Society of Japan, 55(7), 2005â2009.

Authors 4

Takeshi Miyazaki (first)
Shozo Yanagida (additional)
Akira Itoh (additional)
Mitsuo Okahara (additional)

References 18 Referenced 44

{'key': '2024011802162758500_r1'}
10.1021/ic50139a006
10.1021/ic50142a013
10.1246/bcsj.51.3111
10.1021/jo01314a030
{'key': '2024011802162758500_r6'}
10.1246/bcsj.53.1689
{'key': '2024011802162758500_r8'}
{'key': '2024011802162758500_r9'}
{'key': '2024011802162758500_r10'}
{'key': '2024011802162758500_r11'}
{'key': '2024011802162758500_r12'}
10.1021/ja00732a007
{'key': '2024011802162758500_r14'}
{'key': '2024011802162758500_r15'}
{'key': '2024011802162758500_r16'}
10.1246/bcsj.53.2393
{'key': '2024011802162758500_r18'}

Dates

Type	When
Created	19 years, 1 month ago (July 25, 2006, 9:06 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 9:16 p.m.)
Indexed	1 year, 7 months ago (Jan. 19, 2024, 11:39 a.m.)
Issued	43 years, 2 months ago (July 1, 1982)
Published	43 years, 2 months ago (July 1, 1982)
Published Online	19 years, 2 months ago (June 27, 2006)
Published Print	43 years, 2 months ago (July 1, 1982)

Funders 0

None

BibTeX

@article{Miyazaki_1982, title={Synthesis and Alkali-cation Complexing Properties of 12-Crown-4 Derivatives}, volume={55}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.55.2005}, DOI={10.1246/bcsj.55.2005}, number={7}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Miyazaki, Takeshi and Yanagida, Shozo and Itoh, Akira and Okahara, Mitsuo}, year={1982}, month=jul, pages={2005–2009} }

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