Thietanone 1,1-dioxides reactions

Treatment of 3-thietanone 1,1-dioxide with diazomethane, diazoethane, or ethyl diazoacetate gives 3-alkoxythiete 1,1-dioxides, for example, 263. ° A similar reaction occurs with 2-phenyl-3-thietanone 1,1-dioxide and diazomethane. Hydrogenation of the exocyclic double bond in 264 can be accomplished without... 

Thietanone 1,1-dioxide ketals and 3-aminothiete 1,1-dioxides are readily available by cycloaddition of sulfenes to ketene acetals and enamines, respectively (Section V.3.B.). Hydrolysis of these ketals " and the aminothiete sulfones (which are enamines) " " gives 3-thietanone 1,1-dioxides in fair to good yields, as exemplified by the hydrolysis of 133 and 402. Aqueous mineral acids or acidic ion-exchange resins catalyze the reaction. Cis-2-chloro-2,4,4-trimethyl-3-morpholinothietane 1,1-dioxide reacts with N sodium hydroxide to give 38% 2,2,4-trimethyl-3-thietanone 1,1-dioxide, but the trans isomer is recovered unchanged. 3-Methoxy- and 3-ethoxythiete 1,1-dioxide (enol ethers) are also hydrolyzed to 3-thietanone 1,1-dioxide. In several cases, the hydrolysis products are written as enols of the 3-thietanone sulfone. ... 

The 3-thietanone 1,1-dioxide structure proposed for the product of the reaction of azibenzil with sulfur dioxide has been shown by nmr spectroscopy to be incorrect.2,2,4,4-Tetramethyl-3-thietanethione 1,1-dioxide is obtained from the corresponding ketone (69% yield) by treatment with phosphorous penta-sulfide.5 ... 

The reaction of 3-thietanone 1,1-dioxide with methanol to give the hemiketal has been observed by nmr spectroscopy the equilibrium composition is 90% hemiketal-10% ketone.The 2,4-dinitrophenylhydrazone and the p-toluene-sulfonylhydrazone have been reported. 

The a-methylene protons of 3-thietanone 1,1-dioxide are acidic (effervescence is observed in sodium bicarbonate solution). The base-catalyzed reaction of... 

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