100713-68-6

Upstream product

• 532-31-0 silver benzoate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 56-23-5 tetrachloromethane 
• 110-83-8 cyclohexene 
• 94-36-0 dibenzoyl peroxide 
• 7782-50-5 chlorine 

Relevant academic research and scientific papers

Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol

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.

A one-pot synthesis of β-chloro acetates/benzoates from epoxides

A variety of epoxides were converted into β-chloroacetates and benzoates by using TMSCI and the corresponding acid anhydride in the presence of a catalytic amount of Cu(OTf)2.

Organomercury/aluminum-mediated acylative cleavage of cyclic ethers

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

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

Yttrium compounds: New catalysts for the regioselective acylative cleavage of epoxides

The use of Cp2YCl and YCl3 as effective catalysts for the regioselective acylative cleavage of epoxides, especially for the conversion of α,β- epoxyketones to α-chloroenones is described.

Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism

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

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

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.