In the reaction of 2-ethoxy-1,3-oxathiolane with carbonyl compounds in the presence of ZnCl2 or HgCl2, it has been found that only the breaking of the endocyclic bond (C–O or C–S bond) occurs, while the breaking of the exocyclic C–O bond to give the 1,3-oxathiolan-2-ium ion is unfavorable. This behavior is different from that of 2-ethoxy-1,3-dithiolane, in which the breaking of the endocyclic C–S bond occurs by means of HgCl2 and the exocyclic C–O bond, by means of ZnCl2.
The reaction of 2-ethoxy-1,3-dithiolane with carbonyl compounds such as aldehydes and ketones was investigated. The reaction proceeded smoothly in the presence of the HgCl2-catalyst to afford 2-substituted and 2,2-disubstituted 1,3-dithiolanes. The reaction also offers an interesting alternative to the previously reported methods of synthesizing 1,3-dithiolanes which involve the acid-catalyzed reaction of carbonyl compounds with 1,2-ethanedithiol.
Das 1,3‐Oxathiolan (I) reagiert mit den Carbonylverbindungen (II) unter HgCl2‐ oder ZnCl2‐Katalyse zu den entsprechenden 2‐mono‐ oder 2,2‐disubstituierten Oxathiolanen (III); neben (IIIa), (IIIb) bzw. (IIIc) entstehen auch die Bissulfide (IVa), (IVb) bzw. (IVc).
Z‐Ethoxy‐l ,3‐ dithiolan (I) bildet mit Triphenylphosphin (II) und Tetrafluoroborsäure das Phosphoniumsalz (III), das nach Deprotonierung zum Ylid (IV) mit Aldehyden (V), nicht jedoch mit Ketonen, Keten‐S,S‐acetale (VI) und mit Nitrosobenzol das Imin (VIII) ergibt.
The reaction of various phenols with 2-ethoxy-1,3-dithiolane proceeded smoothly in the presence of BF3·Et2O to afford 1,3-dithiolan-2-ylated phenols, which were readily hydrolyzed to the corresponding aldehydes. This process was also extended to N,N-dimethylaniline and indole.
Die Reaktion der Phenole (I) mit dem 2‐Ethoxydithiolan (II) führt in Gegenwart von B‐trifluoridetherat zu den dithiolanylierten Phenolen (III), (IV) und (V), deren Produktenverteilung" durch die Position des Substituenten Rbestimmt wird.
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