10039-14-2Relevant academic research and scientific papers
1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources
Iranpoor, Nasser,Firouzabadi, Habib,Etemadidavan, Elham
, p. 1165 - 1173 (2014)
1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.
Unexpected highly efficient ring-opening of aziridines or epoxides with iodine promoted by thiophenol
Wu, Jie,Sun, Xiaoyu,Sun, Wei,Ye, Shengqing
, p. 2489 - 2491 (2006)
Ring-opening of aziridines or epoxides with iodine promoted by thiophenol afforded β-iodo amines or β-iodo alcohols in good to excellent yields under mild reaction conditions with extremely high efficiency. Georg Thieme Verlag Stuttgart.
A new approach to the synthesis of vicinal iodoperoxyalkanes by the reaction of alkenes with iodine and hydroperoxides
Terent'ev, Alexander O.,Krylov, Igor B.,Borisov, Dmitry A.,Nikishin, Gennady I.
, p. 2979 - 2986 (2007)
A convenient procedure was developed for the synthesis of vicinal iodoperoxyalkanes by the reaction of alkenes with iodine and hydroperoxides. The best results were achieved with the use of excess iodine. The replacement of one iodine atom by hydroperoxid
An Easy and Efficient Epoxide Opening to give Halohydrins using Tin(II) Halides
Einhorn, Cathy,Luche, Jean-Louis
, p. 1368 - 1369 (1986)
Epoxides are readily converted into halohydrins by tin(II) halides in a variety of solvents.
Optical resolution of racemic alcohols via diastereoisomeric supramolecular compound formation with O,O'-dibenzoyl-(2R,3R)-tartaric acid
Kassai, Csaba,Juvancz, Zoltán,Bálint, József,Fogassy, Elemér,Kozma, Dávid
, p. 8355 - 8359 (2000)
O,O'-Dibenzoyl-(2R,3R)-tartaric acid (DBTA) forms a hydrogen bonded supramolecular compound with alcohols. The supra-molecular compound formation is enantioselective for a large number of chiral alcohols, therefore DBTA can be used as resolving agent, also for compounds having no basic group. The condition of the complex formation is that the guest molecule should contain a proton donating group and a fitting aliphatic chain or cycloalkane ring. (C) 2000 Elsevier Science Ltd.
Enzymatic resolution of stereoisomers of 2-iodocyclohexanol
Kolodiazhna,Kolodiazhna,Kolodiazhnyi
, p. 2175 - 2177 (2012)
All four optically active stereoisomers of 2-iodocyclohexanol were synthesized. Their enantiomeric purity was determined upon derivatization with Mosher's acid, absolute configuration have been established by chemical correlation.
Convenient, in situ generation of anhydrous hydrogen iodide for the preparation of α-glycosyl iodides and vicinal lodohydrins and for the catalysis of Ferrier glycosylation
Chervin, Stephanie M.,Abada, Paolo,Koreeda, Masato
, p. 369 - 372 (2000)
(matrix presented) Anhydrous hydrogen iodide is generated in situ by the reaction of solid iodine and a thiol. The HI thus generated has been employed for the efficient preparation of α-glycosyl iodides and vicinal iodohydrins from the corresponding glycosyl acetates and epoxides, respectively, and for Ferrier glycosylation of alcohols and thiols.
Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
Teng, Shenghan,Tessensohn, Malcolm E.,Webster, Richard D.,Zhou, Jianrong Steve
, p. 7439 - 7444 (2018/07/15)
The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.
Regio- and stereoselective co-iodination of olefins using NH4I and Oxone
Durgaiah, Chevella,Naresh, Mameda,Arun Kumar, Macharla,Swamy, Peraka,Reddy, Marri Mahender,Srujana, Kodumuri,Narender, Nama
supporting information, p. 1133 - 1144 (2016/07/22)
A simple, efficient, and environmentally benign protocol for the synthesis of vicinal iodohydrins and iodoesters from olefins using NH4I and Oxone in CH3CN/H2O (1:1) and dimethylformamide (DMF) / dimethylacetamide (DMA), respectively, without employing a catalyst at room temperature is described. Regio- and stereoselective iodohydroxylation and iodoesterification of various olefins with anti fashion, following Markonikov’s rule, was achieved and the corresponding products were obtained in good to excellent yields. In addition, 1,2-disubstituted olefins afforded excellent diastereoselectivity.
Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions
Rao, Dodla S.,Reddy, Thurpu R.,Babachary, Kalvacherla,Kashyap, Sudhir
, p. 7529 - 7543 (2016/08/16)
Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(i) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.
