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Diethylaminosulfur trifluoride (DAST) is the organosulfur compound with the formula Et 2 NSF 3. This liquid is a fluorinating reagent used for the synthesis of organofluorine compounds . [ 1 ] The compound is colourless; older samples assume an orange colour.
The mechanism of fluorination by DAST parallels that of sulfur tetrafluoride. Attack of the hydroxyl group of the substrate on sulfur and elimination of hydrogen fluoride lead to an alkoxyaminosulfur difluoride intermediate. Nucleophilic attack by fluoride, either by an S N 1 [5] or S N 2 [6] pathway, leads to the product. Although clean ...
Introducing the carbon–fluorine bond to organic compounds is the major challenge for medicinal chemists using organofluorine chemistry, as the carbon–fluorine bond increases the probability of having a successful drug by about a factor of ten. [30] Over half of agricultural chemicals contain C-F bonds. A common example is trifluralin. [31]
This was demonstrated in the synthesis of meso-difluorosuccinate from (L)-tartrate and the synthesis of (D)- and (L)-difluorosuccinate from meso-tartrate. [6] Carbonyl compounds generally react with SF 4 to yield geminal difluorides. Reaction times tend to be on the order of hours and yields are moderate. [7]
The final step in the reduction of carboxylic acids and esters is hydrolysis of the aluminium alcoxide. [8] Esters (and amides) are more easily reduced than the parent carboxylic acids. Their reduction affords alcohols and amines, respectively. [9] The idealized equation for the reduction of an ester by lithium aluminium hydride is:
Enantioselective ketone reductions convert prochiral ketones into chiral, non-racemic alcohols and are used heavily for the synthesis of stereodefined alcohols. [1]Carbonyl reduction, the net addition of H 2 across a carbon-oxygen double bond, is an important way to prepare alcohols.
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It finds many uses in organic reactions such as the CBS reduction, Diels-Alder reactions and (3+2) cycloadditions. Proline, a naturally occurring chiral compound, is readily and cheaply available. It transfers its stereocenter to the catalyst which in turn is able to drive an organic reaction selectively to one of two possible enantiomers .