3360-52-9Relevant academic research and scientific papers
One-Pot Twofold Unsymmetrical C-Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp2 to O-Silyl Migration
Wang, Kai,Li, Linjie,Hu, Tianbao,Gao, Lu,Song, Zhenlei
supporting information, p. 12583 - 12595 (2019/10/11)
Twofold unsymmetrical C-Si bond bifunctionalization of 2,6-di(trimethylsilyl) benzyl alcohols has been achieved in one pot via sequential [1,4]-Csp2 to O-silyl migration. The hydroxyl group functions as an "on-off-on" switch to control two successive silyl migrations, and 4,7-dimethyl-o-phenanthroline ligand favors cleavage of the endocyclic C-Si bond. Diverse Csp3/Csp3 or Csp2/Csp3 electrophiles can be installed at the 2- and 6-positions. This approach was used to chemoselectively functionalize the three C-Si bonds of 2,4,6-tri(trimethylsilyl) benzyl alcohol, transforming it into isochroman derivatives. The approach even works as a five-component reaction to construct complex symmetric structures.
Mechanistic insight into the thermal 1,3-chlorine migrations of N-chloroacetanilides under neutral conditions
Cheng, Baoxiang,Xu, Jiaxi
, p. 518 - 525 (2017/05/01)
The mechanistic insight of the thermal 1,3-chlorine migration reactions of N-chloroacetanilides under neutral conditions has been investigated. The results indicate that the 1,3-chorinemigration reaction is initiated by the radical reaction of the homocleavage of the Cl-N bond and subsequent radical combination of the Cl-C bond on the aromatic rings. The radical mechanism was verified by the thermal rearrangement of Nchloro- N-(4-methylphenyl)acetamide in cumene. After generation of hydrochloric acid in the radical mechanism, the migrations occurred through the acid-catalyzed rearrangement as well as the acid-catalyzed Orton reaction. The current results provide a comprehensive understanding on the mechanistic insights in the Orton reaction under different conditions.
A mild and efficient method for the synthesis of a new optically active diallyl selenide and its catalytic activity in the allylic chlorination of natural terpenes
Boualy, Brahim,El Houssame, Soufiane,Sancineto, Luca,Santi, Claudio,Ait Ali, Mustapha,Stoeckli-Evans, Helen,El Firdoussi, Larbi
, p. 3395 - 3399 (2016/05/09)
A mild and convenient method for the synthesis of a new optically active bis(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)selenide 1 from the corresponding bicyclic terpene is described. The structure of the obtained organoselenium compound was establis
Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides
Kiyokawa, Kensuke,Kojima, Takumi,Hishikawa, Yusuke,Minakata, Satoshi
supporting information, p. 15548 - 15552 (2015/11/03)
The iodine-catalyzed decarboxylative amidation of β,γ-unsaturated carboxylic acids with chloramine salts is described. This method enables the regioselective synthesis of allylic amides from various types of β,γ-unsaturated carboxylic acids containing sub
Halofluorination of alkenes using trihaloisocyanuric acids and HF-pyridine
Crespo, Livia T. C.,Ribeiro, Rodrigo Da S.,De Mattos, Marcio C. S.,Esteves, Pierre M.
experimental part, p. 2379 - 2382 (2010/09/04)
Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF-pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%. Georg Thieme Verlag Stuttgart · New York.
Access to cyclopropyl cations via carbene fragmentation
Moss, Robert A.,Chu, Gaosheng
, p. 3321 - 3326 (2007/10/03)
Photolysis of cyclopropyloxychlorodiazirines affords cyclopropyloxychlorocarbenes whose fragmentations provide access to ion pairs, which feature cyclopropyl cations.
CeCl3/NaClO: A safe and efficient reagent for the allylic chlorination of terminal olefins
Moreno-Dorado, F. Javier,Guerra, Francisco M.,Manzano, Francisco L.,Aladro, F. Javier,Jorge, Zacarías D.,Massanet, Guillermo M.
, p. 6691 - 6693 (2007/10/03)
The preparation of allylic chlorides by reaction of terminal olefins with sodium hypochlorite in the presence of cerium trichloride heptahydrate is described. The scope, limitations and synthetic perspectives of the reaction are discussed.
An intriguing effect of Yb(OTf)3-TMSCl in the halogenation of 1,1-disubstituted alkenes by NXS: Selective synthesis of allyl halides
Yamanaka, Masamichi,Arisawa, Mitsuhiro,Nishida, Atsushi,Nakagawa, Masako
, p. 2403 - 2406 (2007/10/03)
A novel protocol to effect the efficient selective halogenation of 1,1-disubstituted alkenes with NXS catalyzed by Yb(OTf)3-TMSCl, which affords the corresponding allyl halides in high yield, including allyl bromide, chloride, iodide and fluori
TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE: AN EFFECTIVE SOURCE OF FLUORIDE ION FOR HALOFLUORINATION OF ALKENES
Albanese, Domenico,Landini, Dario,Penso, Michele,Pratelli, Marco
, p. 537 - 541 (2007/10/02)
Vicinal halofluorides have been prepared from the corresponding alkenes by reaction with a stoichiometric amount of Bu4N+H2F3- as a source of fluoride anion and an excess of an N-halosuccinimide (NXS).The reaction products are obtained in good yields, with a prevalent Markownikoff regiochemistry.Olefins containing hydroxy, epoxy, acetoxy and alkoxy groups do not undergo side reactions under these reaction conditions.
One Step Vinylic Chlorination with Benzeneseleninyl Chloride
Kamigata, Nobumasa,Satoh, Takeshi,Yoshida, Masato,Kobayashi Michio
, p. 345 - 346 (2007/10/02)
The reaction of benzeneseleninyl chloride with olefins in the presence of aluminium chloride or ruthenium(II) phosphine complex under mild conditions was found to give α-chloro-olefins in one step.
