1533-20-6Relevant articles and documents
-
Livingstone,Wilson
, p. 335 (1931)
-
HI gas as a reagent for α-alkylation reaction with two ketone molecules
Matsumoto, Shoji,Koitabashi, Seigo,Otani, Yasuhiko,Akazome, Motohiro
, p. 4320 - 4323 (2015)
To develop the utilization of HI as an 'old but new' reagent, we found that the reaction of acetophenone analogues with HI gas proceeded to give an α-alkylated product, which is derived from the two ketone molecules. It was possible to conduct the reaction in solvent-free and various organic solvents under anhydrous conditions. From the investigation on the reaction mechanism, we proposed that HI acts as an acid and a reducing agent.
Brewster,Kline
, p. 5179,5181 (1952)
Enantioselective conjugate addition of organocuprate using a chiral amidophosphine ligand
Kanai, Motomu,Koga, Kenji,Tomioka, Kiyoshi
, p. 7193 - 7196 (1992)
Based on the concept of a metal differentiating coordination, a new chiral amidophosphine ligand 2 was designed, synthesized, and applied in an enantioselective conjugate addition of lithium dimethylcuprate to chalcone providing the corresponding adduct i
HYDRIDIC REDUCTIONS OF CARBON MONOXIDE TO HYDROCARBONS ON IRON COMPLEXES
Wong, Andrew,Atwood, Jim D.
, p. C9 - C12 (1980)
Treatment of Cp2Fe(CO)4 with LiAlH4 produces CH4, C2H4, C2H6, C3H6, C3H8, C4H8 and C4H10.The exact ratio depends on the amount of LiAlH4 used and on the length of reaction.All reactions were carried out with LiAlD4, confirming that CO is reduced with LiAlH4 as the only hydrogen source.By preparing potential intermediates (CH3FeCp(CO)2, C2H5FeCp(CO)2 and CH3C(O)FeCp(CO)2) and treating them with LiAlD4, we have found evidence for a CO insertion mechanism in chain propagation.Other hydridic reagents were used, the reactivity for the reduction of CO decreases LiAlH4 > NaBH4 > LiEt3BH.
Rational Design of New Dihydrobenzooxophosphole-Based Lewis Base Organocatalysts
Busacca, Carl A.,Haddad, Nizar,Han, Zhengxu S.,Kozlowski, Marisa C.,Qu, Bo,Saha, Anjan,Samankumara, Lalith P.,Schumer, Mac G.,Senanayake, Chris H.,Song, Jinghua J.,Yee, Nathan K.
, p. 587 - 591 (2020)
A series of new dihydrobenzooxophosphole-based Lewis base organocatalysts were designed and synthesized. They are shown to be effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong
Aldol Reactions Promoted by Diethylzinc; the X-ray Crystal Structure and Stereochemistry of Dypnopinacol.
Chaloner, Penny A.,Hitchcock, Peter B.,Langadianou, Eugenia,Readey, Michael J.
, p. 6037 - 6038 (1991)
Diethylzinc reacted with acetophenone to give the aldol dimer, 1,3-diphenyl-2-butene-1-one together with small amounts of dypnopinacol 1-(2-hydroxy-6-methyl-2,4,6-triphenylcyclohex-3-enyl)-1-phenylmethanone.The structure of dypnopinacol was established in an X-ray diffration study.Key Words: Aldol; Diethylzinc, Conjugate reduction; Dypnopinacol
Synthesis of 1,3-diaryl butanones from acetophenones via a tandem reaction
Li, Sida,Laishram, Ronibala Devi,Shen, Guoli,Zhang, Xuexin,Yang, Yong,Ni, Jianxiao,Zhan, Yong,Zhou, Yongyun,Fan, Baomin
, p. 1790 - 1798 (2020)
A tandem reaction for the simple construction of 1,3-diaryl butanones from acetophenones was developed. Anhydrous HI was generated in situ by the promotion of the [Rh]- complex with molecular hydrogen and iodine. The acetophenones undergo aldol reactions
Electron deficient dienes. 2. One step synthesis of a coumarin-fused electron deficient diene and its inverse electron demand Diels-Alder reactions with enamines
Bodwell, Graham J.,Pi, Zulan,Pottie, Ian R.
, p. 477 - 479 (1999)
A coumarin-fused electron deficient diene was prepared by the base- induced reaction of dimethyl glutaconate and salicaldehyde. Its inverse electron demand Diels-Alder reactions with enamines give, after in situ elimination and dehydrogenation, benzocoumarins.
Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide
Matsumoto, Shoji,Marumoto, Hayato,Akazome, Motohiro,Otani, Yasuhiko,Kaiho, Tatsuo
, p. 590 - 599 (2021/03/29)
The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.
Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination
Martins, Bruna S.,Kaiser, Daniel,Bauer, Adriano,Tiefenbrunner, Irmgard,Maulide, Nuno
supporting information, p. 2094 - 2098 (2021/04/05)
A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.
