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

Francisco, C.G. and Gonzalez, C.C. and Kennedy, A.R. and Paz, N.R. and Suarez, E. (2006) Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes. Tetrahedron Letters, 47 (1). pp. 35-38. ISSN 0040-4039

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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.