3,3-dimethyl-thietane-1 -oxide

Wedged octahedral structure for 1 1 adduct of tristdi-pivalomethanato)-europium(III) and 3,3-dimethyl-thietane- 1-oxide... 

Thietane oxides serve as selective solvents for the separation of hydrocarbons. The extracting power of a mixture of water and thietane 1-oxide is considerably greater than that of dimethyl sulfoxide. ... 

Crystallographic measurements have provided additional information about the structure of thietane. The ring of 2-(2,6-dimethylphenyl)imino-3,3-dimethyl-4,4-diphenylthietane is puckered, but in the crystal matrix the rings are more likely to be flattened. 2,4-Diphenylthietane 1-oxide molecules are closely packed with their S=0 bonds nearly parallel to the ring. No intermolecular hydrogen bonding was observed. ... 

The reaction of Af,Af-dimethyl-( )-styrylamine (73) with a halogen-substituted methanesulfonyl chloride allowed the first stereoselective formation of the halogenated thietane 1,1-dioxide 74, which then could be converted to the corresponding thiete sulfone 75 via a Cope elimination of the corresponding AT-oxide. ... 

Thietan-3-one, 2-isopropylidene-4,4-dimethyl-UV, 7, 418 (80JOC4804) lA4- ITiietan-2-one 1-oxide IR, 7, 420 (70JOC584)... 

The basicity of the sulfoxide oxygen has been investigated by observing infrared shifts in protic solvents. ° In this way, it was shown that thietane 1-oxide is more basic than cyclobutanone, but less basic than tetramethylene sulfoxide (thiolane 1-oxide) or pentamethylene sulfoxide (thiane l-oxide). ° Toward phenol, the order of basicity is as follows thiolane 1 -oxide > diethyl sulfoxide > thiepan 1-oxide > dimethyl sulfoxide > thiane 1-oxide > 9-thiabicyclo[3.3.1]nonane 9-oxide > 7-thiabicyclo[2.2.1]heptane 7-oxide > thietane 1-oxide.ThepKaof the conjugate acid of thietane 1-oxide is — 1.92, as determined in aqueous sulfuric acid. =... 

The distribution coefficients for benzene and toluene with thietane 1-oxide was compared with those of other sulfoxides aqueous thietane 1-oxide has a greater extraction capacity than dimethyl sulfoxide. 

Thietane 1-oxides may be reduced to thietanes by iodide ion in acidic mediaby hydrogen sulfide, and by zinc-hydrochloric acid. Thietane 1-oxide is reduced by iodide about four times more rapidly than dimethyl sulfoxide the rate of reduction as a function of ring-size decreases as follows 5 > 4 > 6. The mechanism of reduction by iodide involves slow formation of an iodosulfonium salt 120. The thietane product is unstable in the aeidic medium and was not identified. 

The mechanism proposed for the reduction of thietane 1-oxide by hydrogen sulfide is complex the order of reactivity is ethyl methyl sulfoxide > thiolane 1-oxide > diethyl sulfoxide > dimethyl sulfoxide > thietane l-oxide. ... 

Sultines, Sultones, and Cyclic Sulphates (l 2-Oxathietan 2>Oxides 1,2-Oxa-thietan 2,2-Dioxides, and 1,3,2-Dioxathietan 2,2-Dioxides).—3,3-Dimethyl-4,4-diphenyl-l,2-oxathietan 2-oxide (75), in crystalline form, has been obtained by treatment of the j8-hydroxy-sulphoxide (74) with sulphuryl chloride or A-chlorosuccinimide. It is stable at room temperature for several days but... 

---