103-64-0Relevant articles and documents
Mechanism of dehydrobromination of 1,2-dibromo-1-phenylethane under conditions of phase-transfer catalysis
Suvorova,Panicheva,Mamontova,Belyatskii
, p. 957 - 962 (2003)
Selective dehydrobromination of 1,2-dibromo-1-phenylethane to α-bromostyrene was effected under conditions of phase-transfer catalysis in systems containing KOH, toluene, and tetraalkylammonium bromides. The high selectivity of the catalytic systems originates from stabilization by lipophilic cation of the phase-transfer catalyst of a E1cb-like transition state in the E2 mechanism. In the presence of a catalytic amount of lipophilic alcohols, phenylacetylene was obtained. Substrate activation by alcohol molecules is explained by enhancement of the acceptor power of halogen atoms due to solvation and by increased mobility of hydrogen atoms.
Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides
Gu, Jun,Qiu, Canbin,Lu, Wenbin,Qian, Qun,Lin, Kunhua,Gong, Hegui
, p. 1867 - 1873 (2017)
The use of pyridine as the sole ligand for the reductive vinylation of unactivated secondary alkyl halides under Ni-catalyzed conditions has been developed. Both alkyl- and aryl-substituted vinyl bromides are suitable, in which alkyl-decorated α-alkenyl bromides resulted in the α-products in good results.
THE REACTIONS OF SOME 1,1,1-TRIBROMO-ALKYL SYSTEMS WITH THIOLATE ANIONS
Baird, Mark S.,Hoorfar, Alireza,Mitra, Manjushri
, p. 2509 - 2512 (1981)
Compounds containing a 1,1,1-tribromoethyl group are normally dehydrobrominated by reaction with sodium thiolates.If a 1,1,1-tribromobut-3-ene fragment is present cyclisation to a 2,2-dibromocyclopropylmethyl thioether or rearrangement are also observed.
Transition-metal free synthesis of diaryl vinyl selenides: A simple synthetic approach with high selectivity
Mohan, Balaji,Hwang, Sori,Woo, Hyunje,Park, Kang Hyun
, p. 2699 - 2702 (2014)
A simple, highly efficient synthetic protocol is developed for the synthesis of unsymmetrical diaryl vinyl selenides from diaryldiselenide and β-bromo styrene under transition-metal free conditions in N,N′-dimethyl propylene urea and 130 °C to afford high yields and excellent selectivities. This method provides a new strategy to fabricate a wide variety of important substituted molecular skeletons and an alternative to conventionally used metal salts, additives, and ligands.
Preparation of (Z)-1-halo-1-alkenes and (Z)-1-halo-2-alkoxy-1-alkenes using Cr(II/III) and Fe(0)
Falck,He, Anyu,Bejot, Romain,Mioskowski, Charles
, p. 2652 - 2654 (2006)
Reduction of 1,1,1-trihaloalkanes by Cr(II) or Cr(III) regenerated by Fe(0) in moist tetrahydrofuran at room temperature stereoselectively generates (Z)-1-halo-1-alkenes and (Z)-1-halo-2-alkoxy-1-alkenes in good to excellent yields. Georg Thieme Verlag Stuttgart.
Experimental and theoretical studies on nickel-zinc-catalyzed cross-coupling of gem-dibromoalkenes with P(O)-H compounds
Liu, Liu,Lv, Ye,Wu, Yile,Gao, Xiang,Zeng, Zhiping,Gao, Yuxing,Tang, Guo,Zhao, Yufen
, p. 2322 - 2326 (2014)
A new stereoselective one-pot protocol for the preparation of E-alkenyl-phosphorus compounds under catalysis of an inexpensive nickel-zinc catalyst system has been developed, which provides a potential useful method for C-P bond formation. 31P NMR spectrum and density functional theory calculations were performed to study the reaction mechanism.
Mild regioselective monobromination of activated aromatics and heteroaromatics with N-bromosuccinimide in tetrabutylammonium bromide
Ganguly, Nemai C.,De, Prithwiraj,Dutta, Sanjoy
, p. 1103 - 1108 (2005)
Highly regioselective nuclear bromination of activated aromatic and heteroaromatic compounds has been accomplished using N-bromosuccinimide in tetrabutylammonium bromide. Pre-dominant para-selective monobromination of activated aromatics such as phenols and anilines, rate acceleration of bromination for moderately activated and less reactive substrates on addition of acidic montmorillonite K-10 clay, with or without microwave assistance, are the notable features of this protocol.
Novel system for decarboxylative bromination of α,β-unsaturated carboxylic acids with diacetoxyiodobenzene
Fursule, Ravindra Abhykumar,Patil, Pravin Onkar,Shewale, Bharti Devaji,Kosalge, Satish Bhaskar,Deshmukh, Prashant Krishnarao,Patil, Dilip Ashok
, p. 1243 - 1245 (2009)
A simple and mild method for the conversion of varieties of α,β-unsaturated carboxylic acids to the corresponding bromoalkenes using diacetoxyiodobenzene (IBD) in combination with tetraethyl-ammonium bromide (TEAB) at room temperature is discussed. Advantages of this system are short reaction time, easy work up and gave good to excellent yields.
Brominative Deoxygenation of Some Aldehydes and Ethers
Roman, Ulrich von,Knorr, Rudolf,Behringer, Claudia,Ruhdorfer, Jakob
, p. 260 - 262 (1994)
Three aldehydes (4a-c) are transformed into 1,1-dibromides (6a-c) by 2,2,2-tribromo-2,2-dihydro-1,3,2-benzodioxaphosphole (2).This reagent (2) is also very active in the cleavage of ethers; its reactions may show some features of carbonium as well as of SN2 character.
Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide
Liu, Jiandong,Gong, Hegui,Zhu, Shaolin
supporting information, p. 4060 - 4064 (2020/12/25)
A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.
