Halogen displacement chemistry with silver and alkali metal salts: Preparation of SF5-esters, alcohols, aliphatic olefins, acids and an iodide
It has been found that treatment of SF5-alkyl halides, especially SF5(CH2)(2)Br, with silver salts such as CH3C(O)OAg, p-CH3C6H4SO3Ag, CF3SO3Ag and AgNO3 provides convenient pathways for preparing the following ester compounds: SF5CH2CH2R (R = CH3COO, TosO, CF3SO3, NO3) SF5(CH2)(3)OTos, and SF5(CF2)...
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Published in | Journal of fluorine chemistry Vol. 127; no. 9; pp. 1188 - 1194 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
LAUSANNE
Elsevier
01.09.2006
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Subjects | |
Online Access | Get full text |
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Summary: | It has been found that treatment of SF5-alkyl halides, especially SF5(CH2)(2)Br, with silver salts such as CH3C(O)OAg, p-CH3C6H4SO3Ag, CF3SO3Ag and AgNO3 provides convenient pathways for preparing the following ester compounds: SF5CH2CH2R (R = CH3COO, TosO, CF3SO3, NO3) SF5(CH2)(3)OTos, and SF5(CF2)(4)(CH2)(2)OAc. Important derivatives prepared from these esters include SF5(CH2)(2)OH; SF5(CF2)(4)(CH2)(2)OH. Several alkenes SF5C(Br)=CH2, and SF5CH2(COOCH3)C=CHC(O)OCH3 are obtained using silver salts. The use of alkali metals salts with SF5(CH2)(3)Br is studied and yields SF5(CH2)(3)I; also, a pathway has been developed that extends for SF5(CH2)(3-) the chain by two-carbon atoms and also produces the first SF5-containing malonic acid. Published by Elsevier B.V. |
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ISSN: | 0022-1139 |
DOI: | 10.1016/j.jfluchem.2006.06.010 |