62379-75-3Relevant academic research and scientific papers
Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol
Moghaddam, Firouz Matloubi,Saeidian, Hamdollah,Mirjafary, Zohreh,Javan, Marjan Jebeli,Farimani, Mehdi Moridi,Seirafi, Marjan
experimental part, p. 157 - 163 (2009/09/30)
Efficient synthesis of protected and unprotected chlorohydrins has been achieved by ring opening of epoxides with acetyl/benzoyl chloride and TMSCl using a catalytic amount of ZnO as a reusable catalyst. The applicability of ZnO is further extended by performing the cleavage of the natural product 5,6-epoxysitosterol with acetyl chloride.
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.
REGIOSELECTIVE RING CLEAVAGE OF OXIRANES CATALYZED BY ORGANOTIN HALIDE - TRIPHENYLPHOSPHINE COMPLEX
Shibata, Ikuya,Baba, Akio,Matsuda, Haruo
, p. 3021 - 3024 (2007/10/02)
Vicinal chloroesters are formed in high yield from the reaction of oxiranes and benzoyl chloride in the presence of organotin halide - triphenylphosphine complex with enhanced regioselectivity in oxirane ring cleavage.
