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)...

Full description

Saved in:
Bibliographic Details
Published inJournal of fluorine chemistry Vol. 127; no. 9; pp. 1188 - 1194
Main Authors Winter, R. W., Gard, G. L.
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier 01.09.2006
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
pentafluorothio (SF5)
SF5BR
sulfur hexafluoride derivatives
SF5-esters
silver and nucleophilic substituents
SF5-alcohols
DERIVATIVES
Online AccessGet full text

Cover

More Information
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.
ISSN:0022-1139
DOI:10.1016/j.jfluchem.2006.06.010