18099-26-8Relevant articles and documents
STUDIEN ZUM VORGANG DER WASSERSTOFFUEBERTRAGUNG 64. ELECTROREDUCTIVE SPALTUNG VON ARYLSULFONSAEUREDERIVATEN UND ARYLSULFONEN MIT ALKALI-AMALGAMEN
Horner, Leopold,Schmitt, Rolf-Erhard
, p. 301 - 308 (2007/10/02)
Arylsulfonylchlorides, n-hexylarylsulfonates and di-aryl sulfones (ArSO2Y; Y=Cl, OC6H13, Ar') were cleaved under standard conditions by alkali metal amalgams (M/Hg; M=Li, Na, K) to the corresponding sulfinate salts (ArSO2M) and MY, as shown in Eq. 1.The substrates ArSO2Y in toluene were not cleaved by Li/Hg alone; first on addition of an equimolar amount of i-propanol could conversions of almost 100percent be achieved. (Tables I,II,III).A series of six n-hexylarylsulfonates were studied under standard conditions, to establish the influence of the reaction medium and the amalgam on the course of reaction, (Table II).The sterically hindered arylsulfonates ArSO2OC6H13, (Ar= mesityl, 2,4,6-tri-isopropyl) were "anomalous", i.e. underwent fission at the ring/sulfur bond , as shown by Eq. 2.Table III describes the reductive fission of mesityl-phenylsulfone and dimesitylsulfone.