Sulfene Equivalent

No.135(July 2008)

M1669: Methanedisulfonyl Dichloride (1)

Compound 1 reacts with bases such as Et₃N and produces disulfene 2. This compound 2 easily reacts with diene compounds to form [4+2] cycloadduct 3. Therefore, the compound 2 can be used as a trapping reagent for diene compounds because of this property.¹⁾ In addition, the compound 2 also reacts with α-olefins to form γ-chloroalkanesulfonyl chloride.²⁾

References

1)[4+2] Cycloaddition reaction of dienes with sulfenes
- a)G. Opitz, M. Deissler, K. Rieth, R. Wegner, H. Irngartinger, B. Nuber, Liebigs Ann. 1995, 2151.
- b)G. Opitz, M. Deissler, T. Ehlis, K. Rieth, H. Irngartinger, M. L. Ziegler, B. Nuber, Liebigs Ann. 1995, 2137.
2)Sulfonylation of alkenes
- H. Goldwhite, M. S. Gibson, C. Harris, Tetrahedron 1965, 21, 2743.

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Sulfene Equivalent

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