1004-99-5Relevant articles and documents
Bis-chlorodibutyltin oxide as a new reagent for a mild, versatile and regioselective ring-opening of epoxides
Salomon
, p. 65 - 68 (2001)
A convenient and efficient procedure for the ring-opening of epoxides by means of alcohols and bis-chlorodibutyltin oxide is described. The cleavage of the oxiranes is found to proceed regioselectively under mild reaction conditions. Thus, several haloalkanols, useful intermediates toward biological active molecules, are easily obtained in very good yields.
Efficient synthesis of chlorohydrins: Ionic liquid promoted ring-opening reaction of epoxides and TMSCl
Xu, Li-Wen,Li, Lyi,Xia, Chun-Gu,Zhao, Pei-Qing
, p. 2435 - 2438 (2004)
The environmentally benign, highly efficient synthesis of chlorohydrins by cleavage of epoxides using TMSCl in ionic liquid, bmimPF6, has been studied.
BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: One reagent, two paths
McCluskey, Adam,Leitch, Sarah K.,Garner, James,Caden, Christine E.,Hill, Timothy A.,Odell, Luke R.,Stewart, Scott G.
, p. 8229 - 8232 (2005)
Opening of epoxides can be an effective means by which a variety of functional groups can be incorporated. In this letter, we outline how variation of conditions, in particular, that of solvent and concentration, give rise to different products using the Lewis acid catalyst BiCl3.
Regioselective opening of epoxides catalyzed by Sn (IV). A new method for the synthesis of halohydrins?
Salomon, Claudio J.
, p. 468 - 469 (2000)
The regioselective opening of epoxides with organotin oxides 1 and 2, in presence of halogenated alcohols was developed, yielding the halohydrin derivatives.
Precise Alkoxyamine Design to Enable Automated Tandem Mass Spectrometry Sequencing of Digital Poly(phosphodiester)s
Launay, Kévin,Amalian, Jean-Arthur,Laurent, Eline,Oswald, Laurence,Al Ouahabi, Abdelaziz,Burel, Alexandre,Dufour, Florent,Carapito, Christine,Clément, Jean-Louis,Lutz, Jean-Fran?ois,Charles, Laurence,Gigmes, Didier
, p. 917 - 926 (2021)
A major step towards reliable reading of information coded in the sequence of long poly(phosphodiester)s was previously achieved by introducing an alkoxyamine spacer between information sub-segments. However, MS/MS decoding had to be performed manually to
Trihaloisocyanuric Acid/Triphenylphosphine: An Efficient System for Regioselective Conversion of Epoxides into Vicinal Halohydrins and Vicinal Dihalides under Mild Conditions
De Andrade, Vitor S. C.,De Mattos, Marcio C. S.
, p. 1381 - 1388 (2016)
A new synthetic method has been developed for the regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides by reaction with the system trihaloisocyanuric acid/tri?phenylphosphine in acetonitrile under mild and neutral conditions. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.
A tandem enzyme reaction to produce optically active halohydrins, epoxides and diols
Lutje Spelberg, Jeffrey H.,Van Hylckama Vlieg, Johan E. T.,Bosma, Tjibbe,Kellogg, Richard M.,Janssen, Dick B.
, p. 2863 - 2870 (1999)
The recombinant halohydrin dehalogenase from Agrobacterium radiobacter AD1 was used to obtain enantiomerically pure halohydrins and epoxides by kinetic resolution. By adding an excess of the recombinant epoxide hydrolase from the same organism the reversible conversion was drawn to completion. Halohydrins such as (S)-2,3-dichloro-1-propanol (E>100) and (S)-2-chloro-1-phenylethanol (E=73) were obtained with an enantiomeric excess of higher than 99%. This is a novel biocatalytic route for obtaining enantiomerically pure aromatic halohydrins and epoxides.
Epoxide ring opening catalysed by imidochromium complexes
Leung, Wa-Hung,Wu, Man-Ching,Chim, Joyce L. C.,Yu, Man-Tat,Hou, Hong-Wei,Yeung, Lam-Lung,Wong, Wing-Tak,Wang, Yu
, p. 3525 - 3529 (1997)
tert-Butylimidochromium complexes catalysed ring opening of epoxides by SiMe3(N3) to give azidohydrins in good yields. The proposed mechanism for the chromium-mediated epoxide azidolysis involves the intermediacy of a chromium-azide species which delivers nucleophilic azide to the epoxide substrate. The azido complexes [{Cr(NBut)2Cl}2(μ-N3) 2] 1 and [Cr(ButN=NN=NSiMe3)(N3)Cl2] 2 have been isolated in the reactions of SiMe3(N3) with [Cr(NBut)2Cl2] and [Cr(NBut)Cl3(dme)] (dme = 1,2-dimethoxyethane), respectively. The structure of complex 1 has been established by X-ray crystallography. The mean Cr-N (imide) and Cr-N (azide) distances are 1.605 and 2.061 A, respectively. Reaction of [Cr(NBut)Cl3(thf)2] (thf = tetrahydrofuran) with (S,S)-diop {4,5-[bis(diphenylphosphino)methyl]-2,2-dimethyl-1,3-dioxolane} gave the dimeric complex [{Cr(NBut)Cl3}2{μ(S,S)-diop}], which has been characterised by X-ray crystallography. The Cr-N and Cr-P distances are 1.593(9) and 2.449(4) A, respectively.
Reaction of epoxides with activated DMSO reagent. General method for synthesis of α-chlorocarbonyl compounds: Application in asymmetric synthesis of (3S)-2,3-oxidosqualene
Raina, Sushil,Singh, Vinod K.
, p. 2467 - 2476 (1995)
Reaction of a variety of epoxides with DMSO-Oxalyl chloride in the presence of a catalytic amount of methanol and a base was studied. Disubstituted epoxides gave α-chloroketones in high yields. Aliphatic terminal epoxide underwent opening reaction to provide α-chloroketone as a major product. Trisubstituted epoxides provided α-chloroketones as major products through the formation of more stable carbocation. In case of a homoallylic alcohol, enedione was obtained. The efficiency of the method was shown by applying it to the enantioselective synthesis of (3S)-2,3-oxidosqualene.
Efficient Nucleophilic Cleavage of Oxiranes to Chlorohydrins
Sarangi, Chintamani,Das, Nalin B.,Nanda, Bhagabat,Nayak, Amaendu,Sharma, Ram P.
, p. 180 (1997)
SnCl2*2H2O-Mg and THF-H2O is an efficient system for the conversion of oxiranes into chlorhydrins.
