Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes

1,1,1-Trihaloalkanes of the types R–CCl2I, R–CClBrI, and R–CBr2I belonging to 1,1,1-trihalo-1-deoxy-d-arabinitol series of alditols were prepared and fully characterized by anomeric alkoxyl radical fragmentation of the corresponding 2,2-dihalo-2-deoxy-d-arabino-hexopyranose derivatives. The analogous diiodohalo compounds R–CClI2 and R–CBrI2 could not be prepared by this methodology. The results strongly suggest that the stability of the mixed trihalo alditols decreases with increasing bulkiness of the halogen atoms.