24883-49-6Relevant academic research and scientific papers
Chemoselective Synthesis and Evaluation of β-Oxovinylarsines as an Arsenic Synthetic Precursor
Tay, Wee Shan,Li, Yongxin,Lu, Yunpeng,Pullarkat, Sumod A.,Leung, Pak-Hing
, p. 271 - 278 (2020)
β-Oxovinylarsines are introduced as a stable and highly functionalized bench-top arsenic precursor. Stereoselective syntheses furnished geometrically pure cis- A nd trans-isomers from the same ynone under different conditions. The organic Michael acceptor backbone allowed β-oxovinylarsines to be easily applied to conjugate-addition reactions, and β-oxovinylarsines were reactive to nucleophiles, electrophiles, and transition metals. Unlike other arsenic precursors which are toxic or volatile or have low reactivity, β-oxovinylarsines bear a well-defined organic backbone that confers both stability and known reactivity. Remarkably, β-oxovinylarsines were also compatible with organometallic catalysts and did not decompose or deactivate the catalyst by chelation.
Gold(III)-catalyzed intramolecular furanylation and cyclopropanation of acyclic conjugated enynones
Oh, Chang Ho,Piao, Lanhua,Kim, Ji Hee
, p. 174 - 182 (2013/02/23)
We have developed an efficient cascade gold-catalyzed furanylation- cyclopropanation of acyclic (E)-deca-2,9-dien-4-yn-1-ones and an (E)-undeca-2,10-dien-4-yn-1-one to give 1-(2-furyl)bicyclo[3.1.0]hexanes and a 1-(2-furyl)bicyclo[4.1.0]heptane, respectiv
AlCl3-NaI(NaBr)-t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives
Feray, Laurence,Perfetti, Patricia,Bertrand, Michèle
experimental part, p. 8733 - 8737 (2009/12/28)
(Z)-β-Iodo-propenamides and -β-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and NaI in the presence of t-BuOH in dichlor
Mild stereoselective hydrohalogenation leading to (Z)-halopropenamides at room temperature
Feray, Laurence,Perfetti, Patricia,Bertrand, Michèle P.
scheme or table, p. 89 - 91 (2009/05/30)
Hydroiodination of 2-propynamides leading stereoselectively to (Z)-iodopropenamides was achieved under mild conditions at room temperature by the combined use of zinc iodide and tert-butyl iodide. Similarly, the use of zinc bromide in the presence of tert
A Novel Regio- and Stereospecific Hydrohalogenation Reaction of 2-Propynoic Acid and Its Derivatives
Ma, Shengming,Lu, Xiyan,Li, Zhigang
, p. 709 - 713 (2007/10/02)
2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products.A rationale for the regio- and stereospecifity is briefly discussed.
Stereoselective Conjugate Addition of Halide Anion to Acetylenic Carbonyl Compounds Promoted by Lanthanoid Reagents
Fujisawa, Tamotsu,Tanaka, Akihito,Ukaji, Yutaka
, p. 1255 - 1256 (2007/10/02)
The conjugate addition of halide anion to acetylenic ketones proceeded by the combined use of cerium salts, halotrimethylsilanes and sodium or tetrabutylammonium salts to afford trans-β-halo enones stereoselectively.On the other hand, N,N-diethyl cis-β-haloacrylamides were synthesized from propiolamide.
β-HALOVINYL KETONES: SYNTHESIS FROM ACETYLENIC KETONES
Taniguchi, Mikio,Kobayashi, Shozo,Nakagawa, Masako,Hino, Tohru,Kishi, Yoshito
, p. 4763 - 4766 (2007/10/02)
The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo-or E-β-bromovinyl ketones in trifluoracetic acid, while Z-β-iodo or Z-β-bromovinyl ketones were the major products in acetic acid.Trimethylsilyl iodide and bromide reacted smoothly with acetylenic ketones at -78 deg C to give TMS-allenolates which were readily converted to β-iodo and β-bromovinyl ketones, respectively.
