Alcohols hydrogen fluonde

In l-chloro-2-fluoroacenaphthene [58] and in 2,3-dihalo-2,3-dihydrobenzofuran [59, 60], potassium t rt-butoxide eliminates hydrogen fluonde in preference to hydrogen chloride. trares-2-Chloro-3-fluoro-2,3-dihydrobenzofuran loses hydrogen fluoride quantitatively on treatment with sodamide in tert-butyl alcohol [60] (equation 29). 

Removal of the TBDPS ether in intermediate 71-1 en route to Myxovirescin A1 [Scheme 4.71] gave the desired alcohol 71.2 along with the acyl migration product 71 3.126 With TBAF, a 1 1 mixture of 71,2 and 71,3 was obtained but the rearrangement was minimised to 10% using the hydrogen fluonde-triethylamine complex at room temperature. 

One of the most useful ways of introducing fluorine into organic compounds is the placement of the hydroxyl group in alcohols hydroxy compounds, and carboxylic acids Methyl alcohol reacts with anhydrous hydrogen fluoride at 100 500 °C in the presence of aluminum fluoride [60, 61], zinc fluoride [62] chromium fluonde [63], or a mixture of aluminum and chromium fluondes [64] to give a 20-78% yield of fluoromethane Attempted fluorinations of higher alcohols by this method failed [60]... 

Mixtures of anhydrous hydrogen fluoride and tetrahydrofuran are successfully used as fluorinating agents to convert 1,1,2-trifluoro-l-allcen-3-ols, easily prepared from bromotrifluoroethene via lithiation followed by the reaction with aldehydes or ketones, to 1,1,1,2-tetrafluoro-2-alkenes The yields are optimal with a 5 1 ratio of hydrogen fluoride to tetrahydrofuran The fluorination reaction involves a fluonde lon-induced rearrangement (Sf,j2 mechanism) of allylic alcohols [65] (equation 40)... 

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