Pummerer-Rearrangements are well-known to organic Sulfur chemists to yield internal redox products from C,H-acidic sulfoxides including desoxygenation of sulfur and oxygenation of α-carbon-hydrogen bonds.
Pummerer-Rearrangements are well-known to organic Sulfur chemists to yield internal redox products from C,H-acidic sulfoxides including desoxygenation of sulfur and oxygenation of α-carbon-hydrogen bonds.
1994intermediates intermediates (and their reactions) O 0190
-069Donor Substituted Sulfonyl Carbenes. Part 2. Organothio Sulfonyl Carbenes.-Organothio sulfonyl carbenes, which are prepared in situ by decomposition of ylides like (I) or α-elimination from chloro sulfones of type (IV), can be trapped by enol ethers, styrenes and diazo compounds to afford cyclopropanes such as (III) and (VI) or pyrazoles like (VIII). In the absence of trapping reagents compounds of type (IX) are formed. Treatment of (IVa) with CH2N2 under PTC conditions leads to the cyclopropane (XI) and the Michael adduct (XII) (yield not given) via coupling of the reactive carbanion of (IVa) with electrophilic ketene dithioacetal-S,S-dioxide generated in situ. In addition, it is shown that organothio sulfones such as (IV) react with BuLi and Tms-Cl, I2, or phenyl glyoxal giving carbene Z-dimers like ( XIII) which easily undergo reversible Z/E isomerization. -(SCHANK, K.; ABDEL WAHAB, A.-M. A.; BUEGLER, S.; EIGEN, P.; JAGER, J.; JOST, K.; Tetrahedron 50 (1994) 12,
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