Other Haloacetones

The reaction of methane tricarboxylate with indoline 342 gave the tricyclic derivative 361 which can be transformed to the amide derivatives 362 (97JHC969). Alkylation of the iV-benzyl indoline 360 with pentafluor-oacetone gave 363 which upon debenzylation and subsequent acylation with diketene followed by cyclization gave 364. Other haloacetones were used to prepare different halogenated derivatives (79BEP872311) (Scheme 63). 

Rearrangements arc common in reactions of sulfur tetrafluoride with acetylenic and allylic alcohols. Highly acidic acetylenic alcohols derived from hexafluoroacetone and other haloacetones react readily at ambient temperature to give fluorinated allenes 10 as the sole... 

---