1560-57-2Relevant articles and documents
Iridium-catalyzed H/D exchange at vinyl groups without olefin isomerization
Zhou, Jianrong,Hartwig, John F.
scheme or table, p. 5783 - 5787 (2009/03/11)
(Chemical Equation Presented) Making the switch: The title reaction represents a rare example of olefinic C-H activation without olefin isomerization. The conditions are sufficiently mild so that functional groups such as ketones, esters, nitriles, amines, sulfides, and alcohols are tolerated. This selectivity is demonstrated by deuterium labeling of several complex molecules.
Direct and Regioselective Transformation of α-Chloro Carbonyl Compounds into Alkenes and Deuterioalkenes
Barluenga, Jose,Yus, Miguel,Concellon, Jose M.,Bernad, Pablo
, p. 2721 - 2726 (2007/10/02)
The successive treatment ethyl chloroacetate or chloroacetyl chloride with Grignard reagents and lithium powder leads to symmetrical terminal olefins in a regioselective manner.The best results are obtained with acid chlorides.The influence of the temperature and the reaction time on overall yield of the process are studied; in general, yields are increased by working at low temperature (-60 deg C).Internally substituted olefins are obtained from α-chloro acid chlorides through a similar process.The treatment of α-chloro aldehydes, ketones and carboxylic acid derivatives (esters or acid chlorides) with lithium aluminium hydride or lithium aluminium hydride/aluminium chloride and lithium powder at low temperature (-60 deg C) leads in a regioselective manner to olefins with the same carbon skeleton as the starting carbonyl compound.Reactions with lithium aluminium deuteride lead to incorporation of deuterium at predetermined positions in the alkene.