Synthesis of Isolable Thiirane-2-thione (α-Dithiolactone) from Thioketene S-Oxide

Abstract

Reaction of di-tert-butyl thioketene S-oxide with Lawesson reagent gave 3,3-di-tert-butylthiirane-2-thione in 88% yield. Oxidation of thiirane-2-thione with m-chloroperbenzoic acid afforded 3,3-di-tert-butylthiirane-2-thione S-oxide. The reaction of thiirane-thione was described.

Generation, Reactivity and Uses of Sulfines in Organic Synthesis

“…[19] Finally, the Z-stereochemistry was confirmed by Block et al [20] Recent advances in DART-MS have also allowed the detection of naturally occurring butanethial S-oxide from a related plant, allium siculum. Notably, 3,4-diethyl-1,2-dithietane 1,1-dioxide (7) is formed by a [3,3]-sigmatropic rearrangement. Notably, 3,4-diethyl-1,2-dithietane 1,1-dioxide (7) is formed by a [3,3]-sigmatropic rearrangement.…”

“…[79] On oxidation of a 1-alkenyl 2-alkenyl sulfide to the corresponding sulfoxide the rate of [3,3]-sigmatropic thio-Claisen rearrangement is considerably enhanced, leading to isolable sulfines in excellent yields and E/Z ratios of up to 2:98 depending on the substitution pattern of the sulfoxides (Scheme 30). [79] On oxidation of a 1-alkenyl 2-alkenyl sulfide to the corresponding sulfoxide the rate of [3,3]-sigmatropic thio-Claisen rearrangement is considerably enhanced, leading to isolable sulfines in excellent yields and E/Z ratios of up to 2:98 depending on the substitution pattern of the sulfoxides (Scheme 30).…”

Frustrated Lewis Pair Activation of an N‐Sulfinylamine: A Source of Sulfur Monoxide

“…Crystals suitable for X-Ray diffraction analysis were used to confirm the identity of material 7 as the SO adduct of SIMes (Scheme 3, Figure 4). While related compounds, known as sulfines or thiourea S-oxides, have previously been prepared by methods including dehydrohalogenation of sulfinyl chlorides and oxidation of thiocarbonyl compounds, [23] the present route provides the first example of a synthesis of a sulfine in which a carbene acts as an SO trap.…”

Reaction of Thiofenchone or Thiochamphor with Disulfur Dichloride: Novel Formation of Tricyclic Polysulfanes

“…to give not trisulfane but 10,10-dimethyl-2,3-dithiatricyclo[5.2.1.0 1,5 ]dec-5-ene (5) in 87% yield (Scheme 2).…”