Nucleophilic substitution reactions of difluorormethyl...

Details Nucleophilic substitution reactions of difluorormethyl... Nucleophilic substitution reactions of difluorormethyl...

2006-10-10

2006-10-10

Richter, Johann (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

Reexamination Certificate

active

07119232

ABSTRACT:
(Benzenesulfonyl)difluoromethyl anion, in situ generated from difluoromethyl phenyl sulfone and a base, was found to easily undergo nucleophilic substitution reactions (SN2) with primary alkyl halides, elemental halogens, and perfluoroalkyl halides with good selectivity. The formed (benzenesufonyl)difluoromethylalkanes are useful intermediates for the facile preparation of 1,1-difluoro-1-alkenes and difluoromethylalkanes. Thus, difluoromethyl phenyl sulfone acts as both “CF2═” and “CF2H−” synthons

REFERENCES:
patent: 4837327 (1989-06-01), Stahly
Prakash et al., Nucleophilic Difluoromethylation of Primary Alkyl Halides Using Difluoromethyl Phenyl Sulfone as a Difluoromethyl Anion Equivalent, Org. Lett.; (Letter); 2004; 6(23); 4315-4317.
Prakash et al., Difluoromethyl Phenyl Sulfone, a Difluoromethylidene Equivalent: Use in the Synthesis of 1, 1-Difluoro-1-alkenes (p. 5203-5206), Angew. Chem. Int. Ed. 2004, 43, 5203-5206.
G. Patrick Stahly, “Nucleophilic addition of difluoromethyl phenyl sulfone to aldehydes and various transformations of the resulting alcohols,” Journal of Fluorine Chemistry, 43: 53-66 (1989).

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