43216-12-2Relevant articles and documents
Iodoetherification of unactivated alkenes catalyzed by diphosphine palladium(II) complexes
Doroski, Todd A.,Cox, Matthew R.,Morgan, Jeremy B.
, p. 5162 - 5164 (2009)
A palladium-catalyzed intramolecular iodoetherification of alkenes is reported. The reaction is efficient and highly diastereoselective for disubstituted alkenes. The tether length between the alcohol and alkene can be varied to produce tetrahydrofuran and tetrahydropyran rings. Diphosphine palladium(II) salts are highly active catalysts enabling future studies on the development of an enantioselective process.
A New Easy Method for the Synthesis of Cyclic Halogenoethers and Halogenolactones
Srebnik, Morris,Mechoulam, Raphael
, p. 1070 - 1071 (1984)
Oxidation of halogen salts with m-chloroperbenzoic acid in the presence of 18-crown-6 and of suitable hydroxy or carboxy alkenes leads readily to high yield production of cyclic halogenoethers or halogenolactones.
Highly efficient halogenation of organic compounds with halides catalyzed by cerium(III) chloride heptahydrate using hydrogen peroxide as the terminal oxidant in water
Firouzabadi, Habib,Iranpoor, Nasser,Kazemi, Somayeh,Ghaderi, Arash,Garzan, Atefeh
experimental part, p. 1925 - 1932 (2011/03/18)
In this article a new environmentally friendly catalytic method is described for the efficient monoiodination and bromination of arenes and also iodoetherification and iodolactonization of olefins using hydrogen peroxide as the terminal oxidant. The method is based on using sodium iodide or sodium bromide, hydrogen peroxide (35%) and cerium(III) chloride as an effective catalyst in water at room temperature or under reflux conditions. By this protocol, iodination of anilines proceeded with high regioselectivity at the para position with the formation of small amounts of the ortho isomers. However, bromination of anilines proceeded with absolute regioselectivity to give the para isomers as the sole products in high yields. Iodinations and bromi-nations of m-xylene, toluene, chloro- and bromobenzenes were proceeded with excellent regioselectivity to produce the para isomers as the sole products. Benzene was also halogenated by this catalytic system to give the monohalogenated benzene in good yields. Iodoetherification and iodolactonization of olefins also proceeded easily in high yields at room temperature. However, the bromination of olefins by this protocol failed and the starting materials were detected intact.
Oxone-KI Induced Lactonization and Etherification of Unsaturated Acids and Alcohols: A Formal Synthesis of Mintlactone
Curini, Massimo,Epifano, Francesco,Marcotullio, M. Carla,Montanari, Francesca
, p. 368 - 370 (2007/10/03)
Unsaturated acids and alcohols interact with Oxone and KI in acetonitrile-H2O and undergo iodolactonization and iodoetherification in short times with good yields. The reaction has been used for the formal synthesis of mintlactone starting from isopulegol.