A New Method for the Williamson Ether Synthesis Using t-Alkyl Halides in Nonpolar Solvents

Autor:	Akira Hayashi, Hiromitsu Masada, Fumio Mikuchi, Yasuo Doi
Rok vydání:	1995
Předmět:	chemistry.chemical_classification Aryl Halide General Chemistry Alkali metal Medicinal chemistry Williamson ether synthesis Solvent Hexane chemistry.chemical_compound chemistry Nucleophile Organic chemistry Alkyl
Zdroj:	NIPPON KAGAKU KAISHI. :164-166
ISSN:	2185-0925 0369-4577
DOI:	10.1246/nikkashi.1995.164
Popis:	t is a well-known result that the reactions of t-alkyl halides with alkali metal aryl oxides and alkoxides in protic solvents give olefins (E) almost exclusively. By contrast, we found a new method for the Williamson ether synthesis in the reactions of t-alkyl halides with alkali and alkaline earth metal phenoxides and alkoxides at 60-90° C in nonpolar solvents (hexane and heptane). The yields of t-alkyl phenyl ethers and t-butyl alkyl ethers (SN) were moderate. The selectivity of SN/E was governed by solvent, metal cation (Li+, Na+, K+, Mg2+, Ca2+, Sr2+, and Ba2+), nucleophile, and substrate. The nonpolar solvents were much more effective for the SN reaction than polar solvents.
Databáze:	OpenAIRE
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