120255-98-3Relevant academic research and scientific papers
Organomercury/aluminum-mediated acylative cleavage of cyclic ethers
Luzzio, Frederick A.,Bobb, Rhiana A.
, p. 1851 - 1858 (1999)
Epoxides and tetrahydrofurans are cleaved with concomitant acylation to chloroalkyl esters using a reagent system composed of an organomercurial, aluminum metal and an acid chloride. The cleavage is promoted under mild conditions by a range of readily-available cyclic β-alkoxychloromercurials and acid chlorides. Using mainly tetrahydrofuran and cyclohexene oxide as substrates, the yield of isolated chloroesters ranged from 52 to 96%.
Lanthanoid-catalyzed ring-opening reaction of epoxides with acyl halides
Taniguchi, Yuki,Tanaka, Shintaro,Kitamura, Tsugio,Fujiwara, Yuzo
, p. 4559 - 4560 (2007/10/03)
Eu(dpm)3 [dpm: dipivaloylmethanate] catalyzes the ring-opening reaction of epoxides with acyl halides affording the corresponding 2-haloalkyl esters. The stereochemical course was confirmed as trans-addition in the case of the reaction of cyclo
Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism
Iqbal,Srivastava
, p. 3155 - 3170 (2007/10/02)
Cobalt(II) chloride in acetonitrile catalyses the cleavage of a wide variety of ethers with acyl halides under mild conditions to give the corresponding esters in good yields. Acyclic aliphatic ethers are cleaved to the corresponding ester and chlorides whereas the cyclic aliphatic ethers give rise to the ω-chloroesters. The benzyl ethers can be converted to the corresponding esters along with the formation of benzyl chloride and benzyl acetamide. A comparative study for the cleavage of allyl and benzyl ether has revealed that benzyl ether can be selectively cleaved in presence of the allyl ethers. The oxiranes can be cleaved in highly regioselective manner to the corresponding-β-chloroesters. The vinyl ethers undergo sp2-hybridised carbon-oxygen bond cleavage under these conditions. Based on product analysis, a mechanism involving electron transfer followed by O-acylation and S(N)1 or S(N)2 attack by chloride-ion is discussed.
COBALT CATALYSED REGIOSELECTIVE CLEAVAGE OF OXIRANES WITH ACYLCHLORIDES
Iqbal, Javed,Khan, M. Amin,Srivastava, Rajiv Ranjan
, p. 4985 - 4986 (2007/10/02)
Oxiranes can be cleaved in a regioselective manner with acylchlorides in presence of Cobalt(II) chloride to the corresponding vicinal chloroesters in high yields.
