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

C.G. Francisco, C.C. Gonzalez, A.R. Kennedy, N.R. Paz, E. Suarez

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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.
LanguageEnglish
Pages35-38
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number1
DOIs
Publication statusPublished - 2 Jan 2006

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Sugar Alcohols
Alkanes
Halogens
Derivatives
Atoms
alkoxyl radical

Keywords

  • stability
  • nonfluorinated
  • trihalo-alkanes

Cite this

Francisco, C.G. ; Gonzalez, C.C. ; Kennedy, A.R. ; Paz, N.R. ; Suarez, E. / Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 1. pp. 35-38.
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Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes. / Francisco, C.G.; Gonzalez, C.C.; Kennedy, A.R.; Paz, N.R.; Suarez, E.

In: Tetrahedron Letters, Vol. 47, No. 1, 02.01.2006, p. 35-38.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes

AU - Francisco, C.G.

AU - Gonzalez, C.C.

AU - Kennedy, A.R.

AU - Paz, N.R.

AU - Suarez, E.

PY - 2006/1/2

Y1 - 2006/1/2

N2 - 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.

AB - 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.

KW - stability

KW - nonfluorinated

KW - trihalo-alkanes

U2 - 10.1016/j.tetlet.2005.10.118

DO - 10.1016/j.tetlet.2005.10.118

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VL - 47

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JO - Tetrahedron Letters

T2 - Tetrahedron Letters

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SN - 0040-4039

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