ChemInform Abstract: Ramberg-Baecklund Rearrangement vs. β-Elimination of Haloform from Trichloro and Trifluoromethyl Sulfones.
✍ Scribed by S. BRAVERMAN; Y. ZAFRANI
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 39 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
1998
sulfoxides, sulfones, sulfenes and derivatives sulfoxides, sulfones, sulfenes and derivatives (benzene compounds) Q 0600
24 -084
Ramberg-Baecklund Rearrangement vs. β-Elimination of Haloform from Trichloro and Trifluoromethyl Sulfones. -A new and convenient method for the preparation of trichloro-and trifluoromethyl sulfones (III) and (XIII) is based on a recently published procedure for the preparation of arene sulfinates. Intermediate sulfinates undergo spontaneous rearrangement to the desired sulfones except for (IIIc), where a higher temperature is necessary. In contrast to the corresponding sulfoxides, the sulfones undergo an unusually Ramberg-Baecklund rearrangement affording dichloromethylene products as major compounds. Dichloromethyl sulfones like (V) are formed as minor elimination products. Trifluoro derivative (XIII) shows a complete loss of reactivity even under drastic basic conditions. -(BRAVERMAN, S.; ZAFRANI, Y.;