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2005
Sulfones
Q 0600
04- 098
Difluoromethyl Phenyl Sulfone, a Difluoromethylidene Equivalent: Use in the
Synthesis of 1,1-Difluoro-1-alkenes. — Difluoromethyl phenyl sulfone is used as a
difluoromethylidene equivalent in the novel synthesis of 1,1-difluoro-1-alkenes by a
nucleophilic substitution-elimination procedure. Best results are achieved for primary
alkyl iodides. The present new method can also be applied to primary alkyl bromides
resulting in lower yields whereas for secondary alkyl halides no reaction is observed.
Intermediate alkyl-substituted sulfones (III) undergo β-elimination of the benzenesulfonyl group to afford finally 1,1-difluoro-1-alkenes (IV). — (PRAKASH*, G. K.
S.; HU, J.; WANG, Y.; OLAH, G. A.; Angew. Chem., Int. Ed. 43 (2004) 39,
5203-5206; Dep. Chem., Univ. South. Calif., Los Angeles, CA 90089, USA; Eng.) —
S. Adam
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