Reduction of alkyl and aryl halides with sodium borohydride is well known and has been reported, variously, to proceed via an SnI process,1 an Sn2 process, or nucleophilic attack on halogen2 depending on the structure of the halide. Only recently has evidence appeared suggesting dehalogenation by a free radical path.3 In the course of our recent examination of the reaction of -bromocyclopropyl trifluoroacetates4 with hydride reagents to afford cyclopropanols,6 it became apparent that gem-dibromocyclopropanes are appreciably reactive toward sodium borohydride as well, affording high yields of the corresponding mono-
We1 and others2 have been elaborating the structural and energetic interrelationships among the family of dllHIOO ketones 12d, 22a, 31a, % * 5 4lb z , and k2b. We report here several new interconversions catalyzed by boron trifluoride and a new isomer, R, which appears to be one of the most stable members described to date. 6 0 Scheme I
Die Behandlung des Bromtrifluoracetats (I) mit Na‐tetrahydridoborat in THF liefert das entsprechende Cyclopropanol, das mit Trifluormethansulfonsäureanhydrid das Triflat (II) liefert.
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