Issue 7, 2024
From the journal:

Organic & Biomolecular Chemistry

Alcohol synthesis based on the SN2 reactions of alkyl halides with the squarate dianion†

Kazuto Sato,‡a   Tomoyuki Fujita,‡a   Takashi Takeuchi,a   Takahiro Suzuki, ORCID logo b   Kazutada Ikeuchi ORCID logo §b  and  Keiji Tanino ORCID logo *b  

* Corresponding authors

a Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-0810, Japan

b Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
E-mail: ktanino@sci.hokudai.ac.jp

Abstract

A convenient method has been developed for transforming alkyl halides into the corresponding alcohols via an SN2 reaction. Treatment of an alkyl halide with the squarate dianion at high temperature produces mono-alkyl squarate, and a one-pot basic hydrolysis of the intermediate affords the alcohol in good yield.

Graphical abstract: Alcohol synthesis based on the SN2 reactions of alkyl halides with the squarate dianion

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Article information

DOI
https://doi.org/10.1039/D3OB01507F
Article type
Communication
Submitted
20 Sep 2023
Accepted
10 Jan 2024
First published
11 Jan 2024
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2024,22, 1369-1373

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Alcohol synthesis based on the SN2 reactions of alkyl halides with the squarate dianion

K. Sato, T. Fujita, T. Takeuchi, T. Suzuki, K. Ikeuchi and K. Tanino, Org. Biomol. Chem., 2024, 22, 1369 DOI: 10.1039/D3OB01507F

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