2026-03-13T01:48:57Z https://kanazawa-u.repo.nii.ac.jp/oai

oai:kanazawa-u.repo.nii.ac.jp:00010663 2024-06-20T05:59:56Z 934:935:937

立体障害の大きなアルキル及びアリールネオペンチルエーテルの効率的合成法 An Efficient Synthesis of Hindered Alkyl and Aryl Neopentyl Ethers 政田, 浩光 山本, 哲也 山本, 文将 Copyright © 日本化学会 The Chemical Society of Japan As a rule, the SN2 reactions of neopentyl bromide and tosylate with sodium alkoxides are extremely retarded by steric hindrance, and the yields of alkyl neopentyl ethers are poor because of side reactions such as neopentyl rearrangement, elimination, and decomposition. However, this report deals with a highly selective synthesis of alkyl and aryl neopentyl ethers. We found that the above side reactions were successfully overcome by the use of neopentyl iodide and potassium alkoxide in the mixed solvent of DMSO or DMI- alcohol (1/1-1/2) at 110-140° C. Especially, potassium benzyl oxide and triphenylmethoxide, which are stabilized by delocalization of electron, afforded the corresponding alkyl neopentyl ethers almost quantitatively under optimum conditions. On the other hand, the reactions of alkali metal aryl oxides with neopentyl iodide, tosylate, and mesylate were carried out in DMSO, DMF, and DMI. The desired aryl neopentyl ethers were readily given in substantially quantitative yields. 日本化学会 = The Chemical Society of Japan 1995-12-10 2017-10-03 jpn journal article VoR http://hdl.handle.net/2297/37652 https://kanazawa-u.repo.nii.ac.jp/records/10663 10.1246/nikkashi.1995.1028 http://www.chemistry.or.jp/ https://www.jstage.jst.go.jp/browse/nikkashi/-char/ja/ http://ci.nii.ac.jp/naid/10001684704/ AN00186595 0369-4577 日本化学会誌 : 化学と工業化学 = Journal of the Chemical Society of Japan : chemistry and industrial chemistry 1995 12 1028 1031 https://kanazawa-u.repo.nii.ac.jp/record/10663/files/TE-PR-MASADA-H-1028.pdf application/pdf 1.1 MB 2017-10-03