A highly efficient, mild, and selective cleavage of β-methoxyethoxymethyl (MEM) ethers by cerium(III) chloride in acetonitrile

A highly selective cleavage of MEM ethers has been achieved in high yields using CeCl<SUB>3</SUB>·7H<SUB>2</SUB>O in refluxing acetonitrile under mild and neutral reaction conditions. The method is very rapid and compatible with other hydroxyl protecting groups such as Bn, TBDPS, Ac, Me, Tr, PMB, benzylidene, THP, MOM, BOM, and NHAc present in the substrate

Highly regioselective ring opening of epoxides and aziridines using cerium(III) chloride

A wide variety of epoxides and aziridines were converted to the corresponding β-halohydrins and β-haloamines using cerium(III) chloride and the cerium(III) chloride/NaI system in acetonitrile. The reactions were highly regioselective and efficient with excellent yields under mild and neutral reaction conditions

Ring opening of epoxides and aziridines with sodium azide using Oxone<SUP>&#174;</SUP> in aqueous acetonitrile: a highly regioselective azidolysis reaction

A wide variety of epoxides and aziridines were converted to the corresponding &#946;-azido alcohols and &#946;-azido amines with sodium azide using Oxone<SUP>&#174;</SUP> in aqueous acetonitrile. The reactions were highly regioselective and efficient with excellent yields at room temperature under mild reaction conditions

Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products

Oxidation of bis(2-hydroxy-1-naphthyl)methane with DDQ gave the novel dispiro compounds cis- and trans-I together with spiro compounds II (n = 1, 2). The structures of I were detected by spectral methods. Hydrogenation of I gave 1-(2-hydroxy-1-naphthyl)methyl-2-(2-hydroxy-1-naphthyloxy)naphthalene by $C-C$ bond cleavage. A number of analogs of I were prepared similarly. A reaction mechanism involving quinol ether intermediates is proposed

Reaction of spironaphthalenones with hydroxylamine: Part I. A reinvestigation of the mechanism

Spironaphthalenones 1b-g on reaction with hydroxylamine hydrochloride gave the expected pyrrolotropones 2b-g. Furanotropone 6, postulated as an intermediate in the formation of pyrrolotropones, remained unchanged on reaction with hydroxylamine hydrochloride in ethanol. Reaction of unsymmetrical spironaphthalenones 1h-o with NH2OH.HCl gave the rearranged pyrrolotropones 2h-o