New ω-substituted anisoles: III. Aryloxymethyl halides: Their preparation and reactions

Autor:	H. T. Zwartouw, H. J. Barber, M. B. Green, R. F. Fuller
Rok vydání:	2007
Předmět:	chemistry.chemical_classification Sodium Halide Phosphorus pentachloride chemistry.chemical_element Medicinal chemistry chemistry.chemical_compound Sodium phenoxide Thionyl chloride chemistry Organic chemistry Phenol Sodium thiocyanate Alkyl
Zdroj:	Journal of Applied Chemistry. 3:266-274
ISSN:	1934-998X 0021-8871
DOI:	10.1002/jctb.5010030605
Popis:	Aryloxymethanesulphonic acids, ArO·CH2·SO3H, or their salts react readily at room temperature with chlorinating agents such as phosphorus pentachloride or thionyl chloride. Sulphur dioxide is eliminated and the hitherto unknown aryloxymethyl chlorides, ArO·CH2Cl, are formed in high yield. These chlorides readily undergo a variety of metathetical reactions, e.g. with sodium alkoxides to form aryloxymethyl alkyl ethers, with sodium phenoxide to form bisaryloxymethanes, with sodium salts of carboxylic acids to form aryloxymethyl esters, with sodium cyanide to form aryloxyacetonitriles, with sodium thiocyanate to form aryloxymethyl thiocyanates, with potassiophthalimide to form aryloxymethyl-phthalimides, and with tertiary amines to form quaternaryaryloxymethyl ammonium salts. With primary and secondary amines they break down to the parent phenol, and with ethyl sodiomalonate they give bisaryloxymethane and methylenebismalonic ester.
Databáze:	OpenAIRE
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