General Characteristics The original Julia olefination procedure was somewhat inconvenient as it required three operations (nucleophilic addition, acetylation, and elimination using toxic Na ...
Author Archive
Organotrifluoroborate Salts
General Characteristics Organotrifluoroborate salts (R-BF3–) are stable towards heat, air, and moisture, and are convenient crystalline reagents. Because of the tetra-coordinated borate ...
Saucy-Marbet Rearrangement
General Characteristics Propargyl vinyl ethers undergo thermal or catalylzed [3,3]-sigmatropic rearrangement to give the corresponding ketoallenes. For chiral compounds, the stereochemistry of the ...
Zinc Borohydride
General Characteristics Zinc borohydride (Zn(BH4)2) is prepared from ZnCl2 and NaBH4. In addition to being used for 1,2-reduction of α,β-unsaturated carbonyl compounds, it can selectively reduce ...
Mukaiyama-Suzuki Glycosylation
General Characteristics The use of fluorinated sugars as glycosyl donors in glycosylation reactions was first reported by Mukaiyama. The original method employed a cationic tin-based Lewis acid as an ...
Woollins’ Reagent
General Characteristics 2,4-Diphenyl-1,3-diselenadiphosphetane-2,4-diselenide is called the Woollins’ reagent. In a similar way that the Lawesson’s reagent is used to convert carbonyl groups to the ...
Semmler-Wolff Reaction
General Characteristics The synthesis of anilines from the corresponding cyclohexenone oximes is known as the Semmler-Wolff reaction. Due to the competing Beckmann rearrangement, yields tend to be ...
Nitroxyl Radical Oxidation Catalysts
General Characteristics Alkylated hydroxylamines are easily oxidized by oxygen in the air. When there is a proton on the carbon α to the nitrogen, hydroxylamines are oxidized to nitrones. However, ...
Vanadyl(IV) acetylacetonate
General Characteristics Vanadyl acetylacetonate (VO(acac)2) is used as a catalyst for epoxidation of allylic alcohols (with the use of tert-butyl hydroperoxide as the re-oxidant). The directing ...
Shenvi Isonitrile Synthesis
General Characteristics Shenvi reported recently that isonitriles can be prepared by substitution of tertiary alcohols using TMSCN with the inversion of stereochemistry. Isonitriles can be regarded ...