13706-68-8Relevant academic research and scientific papers
Stereoselective One-Pot Synthesis of cis-1,2-Dicyanoalkenes from 1,1-Bis(benzenesulfonyl)alkenes and KCN
Zhang, Yue,Wei, Yi,Li, Shen,Ma, Jun-An
, p. 199 - 203 (2019/01/04)
An efficient synthesis of cis-1,2-dicyanoalkenes by the reaction of 1,1-bis(benzenesulfonyl)alkenes with KCN was developed. This reaction was conducted in the presence of tetrabutylammonium bromide and NH4Cl/K3PO4 under phase-transfer conditions. A series of cis-1,2-dicyanoalkenes were obtained in good to high yields. Further transformation of the obtained product allows for access to imide and dicarboxylic acid compounds.
Tetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag
Guo, Shuhui,Mi, Xueling
supporting information, p. 2881 - 2884 (2017/07/11)
Tetraarylphosphonium inner-salts (TAPIS) have been designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst has been successfully applied in Michael addition, cyanation and trifluoromethylation reactions.
Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride
Kiyokawa, Kensuke,Nagata, Takaya,Hayakawa, Junpei,Minakata, Satoshi
supporting information, p. 1280 - 1285 (2015/02/19)
A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.
The reactivity of TMSN3 with ruthenium cyclopropenyl complexes containing different ligands and different substituent at Cγ
Sung, Hui-Ling,Hsu, Hsiu-Ling
experimental part, p. 1280 - 1288 (2011/04/25)
Ruthenium vinylidene complexes 2a-2c containing indenyl and bidentate dppe ligands can be obtained in efficient yields. Treatment of the cationic ruthenium vinylidene complexes with n-Bu4NOH in acetone yields the neutral cyclopropenyl products (η5-C9H7)(dppe)Ru- CC(Ph)CHR (3) (3a, R = Ph; 3b, R = CN; 3c, R = p-C6H4-CN) via the deprotonation reaction. Reaction of complexes 3a and 3c with Me 3SiN3 (TMSN3) the N-coordinated complexes 4a and 4c can be obtained as stable products. Complex 3b containing CN group at Cγ in the cyclopropenyl ring reacts with TMSN3 yielded the tetrazolate complex 5b. Similar cyclopropenyl products containing indenyl and two triphenylphosphine ligands 3′ can also be synthesized. Reaction of complex 3b′ with TMSN3 also yielded the tetrazolate complex as the major product. And the minor products are [Ru]-N3 and organic compound 6b. Reaction of 3a′ and 3c′ with TMSN3 yielded [Ru]-N3. The corresponding organic products can also be obtained via the N3- attacking the metal center in the N-coordinated complexes 4a′ and 4c′.
Facile one-pot synthesis of 2-aryl-substituted nitriles and 2-aryl-3-keto nitriles via benzyne reaction
Kamila, Sukanta,Koh, Benjamin,Biehl, Edward R.
, p. 3493 - 3507 (2007/10/03)
2-Aryl-substituted nitriles were prepared in good to excellent yields in a one-pot reaction by the reaction of benzyne, generated using neutral conditions from (phenyl)[o-(trimethylsilyl)-phenyl]iodonium triflate, and 2-lithionitriles. 3-Keto nitriles substituted at the 2-position were obtained in good yields when these reactions were trapped with acid chlorides. The mechanism of the benzyne reaction in terms of a N-lithiobenzocyclobutanimine intermediate is discussed. Copyright Taylor & Francis Group, LLC.
Reductive Arylation of Maleic and Fumaric Acid Derivatives by Arenediazonium and Titanium(III) Salts
Citterio, Attilio,Cominelli, Alberto,Bonavoglia, Francesco
, p. 308 - 309 (2007/10/02)
The titanium(III)-induced decomposition of substituted benzenediazonium salts in the presence of maleic and fumaric acids, alkyl esters, amides, and nitriles gives the corresponding arylsuccinic acid derivatives.
REDUCTION OF α - SUBSTITUTED SUCCINONITRILES WITH DIISOBUTYLALUMINIUM HYDRIDE: A FACILE METHOD FOR THE SYNTHESIS OF 3-SUBSTITUTED PYRROLES
Babler, James H.,Spina, Kenneth P.
, p. 1659 - 1660 (2007/10/02)
Treatment of four representative α-substituted succinonitriles (2) with diisobutylaluminium hydride, followed by hydrolysis of each reaction mixture with aqueous sodium dihydrogen phosphate, afford 3-substituted pyrroles (4) in approximately 50percent yie
