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.
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.
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.
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Nakai,H.,Kurono,M.
, p. 995 - 998 (1977)
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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.
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.
Facile Conversion of Epoxides to Chlorohydrins with Titanium(IV) Chloride/1,8-Diazabicycloundec-7-ene
Spawn, Carol-Lynn,Drtina, Gary J.,Wiemer, David F.
, p. 315 - 317 (1986)
A series of epoxides has been converted to the analogous chlorohydrins by treatment with titanium(IV) chloride and 1,8-diazabicycloundec-7-ene.This procedure tolerates acetal protecting groups normally labile to aqueous acids, and when used in conjunction with the Sharpless epoxidation protocols, it allows the preparation of chiral chlorodiols selectively protected at one hydroxy group.
Polyvinylpyrrolidone/thionyl chloride as a new polymeric reagent for facile conversion of epoxides to β-chlorohydrins
Tamami, Bahman,Ghazi, Iraj,Mahdavi, Hossein
, p. 3725 - 3731 (2002)
Epoxides undergo rapid ring opening with cross-linked polyvinylpyrrolidone/thionyl chloride complex, under mild reaction condition to afford chlorohydrins in high yields.
Selective monochlorination of unsymmetrical vicinal diols with chlorinated iminium chlorides
Li, Chengyang,Li, Xiaotong,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
, (2020/03/23)
Chlorinated iminium chlorides have been identified to promote the highly efficient and selective mono-chlorination of unsymmetrical vicinal diols. Vilsmeier reagent, namely, (chloromethylene)dimethyliminium chloride, enables highly reactive and regioselective chlorination of 1,2- and 1,3-diols featured one secondary benzylic hydroxy group and one primary aliphatic hydroxy group to give the corresponding 1,2- and 1,3-chlorohydrins. Viehe's salts (α,α-dichloro iminium salts) exhibit excellent reactivity and good selectivity for vicinal diols to give the corresponding chlorohydrin carbamates via a cyclic intermediate in situ. The chlorination protocols tolerate diverse functional groups, including halogens, naphthalene rings, nitro, and cyano. Moreover, the optical purity of chiral diols could be retained during this chlorination reaction.
Visible-light-triggered Catalytic Halohydrin Synthesis from Epoxides and Trichloroacetonitrile by Copper and Iron Salts
Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Suga, Hiroyuki
supporting information, p. 1469 - 1471 (2019/12/02)
Preparation of vicinal halohydrins, in which copper or iron chlorides catalyze the ring-opening reaction of epoxides with visible light effectively, is described. The use of trichloroacetonitrile as a halogen source enables catalytic HCl generation under the mild conditions. This method can also be applied to the aziridine ring-opening reaction.
