Application of Alkoxy-λ6-sulfanenitriles as Strong Alkylating Reagents

Autor:	Wei Hao, Tiaoling Dong, Toshiaki Yoshimura, Youko Wakai, Takayoshi Fujii
Rok vydání:	2004
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Nucleophile Chemistry Thiophenol Heteroatom Alkoxy group SN2 reaction Reactivity (chemistry) General Medicine Alkylation Medicinal chemistry Alkyl
Zdroj:	ChemInform. 35
ISSN:	1522-2667 0931-7597
Popis:	Alkoxy-λ6-sulfanenitriles were found to be versatile alkylating reagents toward various nucleophiles bearing at least one proton such as methanol, phenol, thiophenols, carboxylic acids, p-toluenesulfonic acid, hydrochloric acid, and primary and secondary amines. Reactivity of the alkoxy group of the λ6-sulfanenitriles showed an opposite trend to the usual SN2 character, i.e. Me (1a), Pr (1b), and Bu (1d) ≪ i-Pr (1c). In the presence of p-TsOH, alkyl tosylates were predominantly formed instead of the alkylation products of nucleophiles. In addition, even a sterically hindered substrate, neopentyloxy-λ6-sulfanenitrile, was found to undergo an SN2 reaction toward thiophenol without any rearrangement product to give neopentyl phenyl sulfide in good yield. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:193–198, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20006
Databáze:	OpenAIRE
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