Halogen displacement chemistry with silver and alkali metal salts: Preparation of SF 5-esters, alcohols, aliphatic olefins, acids and an iodide
For the first time it was found that silver oxy-salts can be used with SF 5CH 2CH 2Br and other SF 5-aliphatic and fluoroaliphatic systems resulting in new pathways and compounds for SF 5-containing esters, alcohols and olefins. Also, a two-carbon chain extension is possible with the potassium salt...
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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 |
Elsevier B.V
2006
|
Subjects | |
Online Access | Get full text |
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Summary: | For the first time it was found that silver oxy-salts can be used with SF
5CH
2CH
2Br and other SF
5-aliphatic and fluoroaliphatic systems resulting in new pathways and compounds for SF
5-containing esters, alcohols and olefins. Also, a two-carbon chain extension is possible with the potassium salt of malonic ester; the first SF
5-malonic acid is reported. The unique iodide, SF
5(CH
2)
3I has been prepared.
It has been found that treatment of SF
5-alkyl halides, especially SF
5(CH
2)
2Br, with silver salts such as CH
3C(O)OAg,
p-CH
3C
6H
4SO
3Ag, CF
3SO
3Ag and AgNO
3 provides convenient pathways for preparing the following ester compounds: SF
5CH
2CH
2R (R
=
CH
3COO, TosO, CF
3SO
3, NO
3), SF
5(CH
2)
3OTos, and SF
5(CF
2)
4(CH
2)
2OAc. Important derivatives prepared from these esters include SF
5(CH
2)
2OH; SF
5(CF
2)
4(CH
2)
2OH. Several alkenes SF
5C(Br)
CH
2 and SF
5CH
2(COOCH
3)C
CHC(O)OCH
3 are obtained using silver salts. The use of alkali metals salts with SF
5(CH
2)
3Br is studied and yields SF
5(CH
2)
3I; also, a pathway has been developed that extends for SF
5(CH
2)
3− the chain by two-carbon atoms and also produces the first SF
5-containing malonic acid. |
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ISSN: | 0022-1139 1873-3328 |
DOI: | 10.1016/j.jfluchem.2006.06.010 |