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

doi:10.1016/j.tetlet.2005.10.118

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 journal › Article › peer-review

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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.

Original language	English
Pages (from-to)	35-38
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2005.10.118
Publication status	Published - 2 Jan 2006

Keywords

stability
nonfluorinated
trihalo-alkanes

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Kennedy, A.
Pure And Applied Chemistry
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title = "Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes",

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.",

keywords = "stability, nonfluorinated, trihalo-alkanes",

author = "C.G. Francisco and C.C. Gonzalez and A.R. Kennedy and N.R. Paz and E. Suarez",

year = "2006",

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doi = "10.1016/j.tetlet.2005.10.118",

language = "English",

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journal = "Tetrahedron Letters",

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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

M3 - Article

SN - 0040-4039

VL - 47

SP - 35

EP - 38

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

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

Abstract

Keywords

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