19347-73-0Relevant articles and documents
On the reactions between phosphorus pentachloride and lactones
Ismaili, Valeh Mehralioglu,Aydin, Adnan,Kantaeva
, p. 137 - 142 (1999)
Reactions between PCl5 and substituted or unsubstituted β-, γ- and ε-lactones have been investigated. Although γ-butyrolactone substituted at α-position with an alkyl radical has given phosphorylated products of both cyclic ethers and chlorinated carboxylic acid chlorides along with γ-chlorobutanoic acid chloride, halogen substituted γ-butyrolactone such as α-bromo-γ-butyrolactone yielded α-bromo-γ-chlorobutanoic acid chloride in similar manner with β-propiolactone which gives β-chloropropionic acid chloride. The nature of radicals present at γ-position also affects the reaction products. Methyl or heptyl radicals yielded different products; in the latter case phosphorylated products were not isolated. The reaction pathway of ε-caprolactone with PCl5 is changed by the temperature of the reaction mixture. It reacts at 20-30°C to give α,α-dichlorooxepane and ε-chlorohexanoic acid chloride, while a phosphorylated product was observed at 60-70°C. Possible mechanisms of these reactions are discussed.
Catalytic asymmetric reductive acyl cross-coupling: Synthesis of enantioenriched acyclic α,α-disubstituted ketones
Cherney, Alan H.,Kadunce, Nathaniel T.,Reisman, Sarah E.
supporting information, p. 7442 - 7445 (2013/06/27)
The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a NiII/bis(oxazoline) catalyst in the presence of Mn0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.
Free Radical Substitution. Part 37. The Effect of Solvent on the Atomic Chlorination of 1-Substituted Butanes and Related Compounds
Potter, Alan,Tedder, John M.
, p. 1689 - 1692 (2007/10/02)
Experimental results reported in this paper show that the relative selectivity of atomic chlorination of 1-substituted butanes and related compounds is greatly influenced by the phase and by solvents.Solvents can be divided into three classes: (a) inert, (b) solvents which decrease the selectivity, and (c) solvents which increase the selectivity.The second group solvate the transition state and the third group solvate the chlorine atoms.
