36220-92-5Relevant articles and documents
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.
The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters
Nakamura, Kaoru,Takenaka, Keishi
, p. 415 - 422 (2007/10/03)
Polyphenols, such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase Amano AH.
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
A new synthetic method for haloalkyl carboxylic esters from the radical ring cleavage of cyclic acetals with haloform
Hai-Xia, Lin,Liang-Heng, Xu,Nai-Ju, Huang
, p. 303 - 306 (2007/10/03)
A one-pot reaction of cyclic acetals with haloform catalyzed by AIBN(2,2'-azobisisobutyronitrile) provides a novel convenient way to prepare directly haloalkyl carboxylic esters in good yields.
Reaction of Epoxides with Chlorocarbonylated Compounds Catalyzed by Hexaalkylguanidinium Chloride
Gros, P.,Perchec, P. Le,Senet, J. P.
, p. 4925 - 4930 (2007/10/02)
Silica-supported guanidinium chloride (PBGSiCl) exhibits efficient chemo- and regiospecific catalytic activity in the ring opening of epoxides with various electrophiles.This reaction allows the preparation of β-chloro esters and β-chloro chloroformates in high yield under neutral conditions which offer product stability and ease of product isolation.
Reactions of 1,3-dioxolanes with Iodine Monochloride: Formation of Chlorohydrin Esters and Diol Monoesters
Glass, Beverley D.,Goosen, Andre,McCleland, Cedric W.
, p. 2175 - 2182 (2007/10/02)
2-Mono-substituted 1,3-dioxolanes are oxidised by iodine monochloride to the appropriate 2-substituted 1,3-dioxolan-2-ylium ions, whose stability is dependent upon the presence and nature of substituents on C-4 and C-5.Some dioxolanylium ions are labile and under the reaction conditions afford chlorohydrin esters, with inversion of configuration taking place at the ring carbon attacked by chloride.Others are stable under the reaction conditions and may be converted on aqueous workup to diol monoesters with retention of configuration at C-4 and C-5.The effect of substituents and reaction conditions on these competing reactions are described.The stereo- and regio-chemistry of both hydroxy- and chloro-ester formation was confirmed through NMR studies, which necessitated the prior detailed analysis of the 1H and 13C spectra associated with the acyloxy sidechains of the relevant esters.
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.
Reaction of 1,3-dioxolans with Iodine Monochloride: the Scope and Mechanism of Formation of 1,3-dioxolan-2-ylium Dichloroiodates(I)
Goosen, Andre,McCleland, Cedric W.
, p. 977 - 983 (2007/10/02)
Treatment of a series of 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolanes with iodine monochloride afforded the appropriate 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium dichloroiodate(I) salts in excellent yields.In contrast to the stable 2-aryl-substituted salts, the 2-alkyl and unsubstituted derivatives were relatively labile.While 2-phenyl-1,3-dioxolan and 2-phenyl-1,3-dioxan afforded low yields of unstable salts,crystalline products could not be isolated from 4,5-disubstituted dioxolans.The reaction was inhibited by electron-withdrawing 4- and 5-substituents.From a study of the effects of photolysis and added iodine, the mechanism is proposed to involve a hydride ion transfer.Possible reasons for the formation of dichloroiodate(I) rather then monohalide salts, are outlined.The stability of the 2-aryl-substituted salts is dicussed in terms of charge distribution in the cation and possible aryl-anion interactions.
