Fluorination Diethylamino sulfur trifluoride

When the 2-hydroxy group of a monosaccharide reacts with (diethylamino)sulfur trifluoride (DAST), quantitative and stereoselective rearrangements are observed (K.C Nico-laou, 1986). This reaction may simultaneously introduce fluorine to C-1 and a new oxygen, sulfur, or nitrogen residue to C-2 with inversion of configuration. 

In the reaction of benzyl 3-azido-5-0-benzoyl-3,6-dideoxy-a-L-talofuranoside (4) with (diethylamino)sulfur trifluoride (DAST) the anomeric alkoxyl group migrated to the C-2 position and a fluorine atom entered into C-l from the P-side to give the 2-benzyl ether 5 having P-l-galacto configuration [101]. Methyl 2-0-benzoyl-5-0-... 

The reaction proceeds with inversion of configuration. The reagent has been compared with other fluorinating reagents for the preparation of 2-fluorooctane. In this case, the highest yield (40%) is obtained with KF or diethyl(2-chloro-l,l,2-trifluoroethyl)amine (5, 26), but the highest optical yields are obtained with 1 (100%) and (diethylamino)sulfur trifluoride (97.6%, 6, 183-184). ... 

Gree and co-workers have found that bicyclic epoxy alcohols when treated with diethylamino sulfur trifluoride (DAST) can undergo a ring expansion via C-C bond cleavage of the oxirane ring to provide fluorinated cyclic vinyl ethers (Table 17) <20020L451>. 

FLUORINATION Acetyl hypofluorite. Cesium fluoroxysulfate. (Diethylamino)-sulfur trifluoride. 

MJ. Robins, K.B. Mullah, S.F. Wnuk, and N.K. Dailey, Nucleic acid related compounds. 73. Fluorination of uridine 2 -thiocthers with xenon difluoride or (diethylamino)sulfur trifluoride. Synthesis of stable 2 -[alkyl(or aryl)sulfonyl]-2 -deoxy-2 -fluorouridines,/. Org, Chem, 57 2357 (1992). 

Diethylaminosulfur trifluoride (DAST. 1), an established fluorinating agent, was first synthesized in 1970 from (diethylamino)triinethylsilane and sulfur tetrafluoride. ... 

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