A Facile Method of Synthesis of α-Acetylenic Ketones

Shergina, S. I.; Sokolov, I. E.; Zanina, A. S.

doi:10.1070/mc1994v004n06abeh000415

Cited by 7 publications

(9 citation statements)

References 5 publications

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“…The starting material ReH 5 (PMe 2 Ph) 3 was prepared following the procedure described in the literature . 3- tert -Butyldeca-1,4-diyn-3-ol was prepared from ethynylmagnesium bromide and 2,2-dimethyldec-4-yn-3-one . All other reagents were used as purchased from Aldrich Chemical Co. or Strem Chemical Co.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Shift Reactions of Rhenium Hydrido Carbyne Complexes

et al. 2012

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Rhenium hydrido carbyne complexes Re(CCHC(CMe3)CCR)HCl(PMe2Ph)3 (R = H, n-pentyl) undergo 1,2-hydrogen shift reactions from the metal to the carbyne carbon atom to give complexes Re(HCCHC(CMe3)CCR)HCl(PMe2Ph)3, which have two isomeric forms, namely, a metallabicyclo[3.1.0]hexatriene complex, in which the chloride is cis to the metal-bonded CH, and an alkyne–carbene complex, in which the chloride is trans to the metal-bonded CH. In contrast, a similar transformation does not occur for the analogous complex Re(CCHC(CMe3)CCSiMe3)HCl(PMe2Ph)3, which has a SiMe3 group on the CC moiety. A computational study suggests that the difference in the reactivity of the hydrido carbyne complexes is related to steric effects in the corresponding hydride-shift products. Formation of Re(HCCHC(CMe3)CCSiMe3)HCl(PMe2Ph)3 is not favored, mainly due to the steric interactions of the SiMe3 group with CMe3 and one of the phosphine ligands in the resulting metallabicyclo[3.1.0]hexatriene complex, and of the SiMe3 group with the chloride ligand in the resulting alkyne–carbene complex.

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Section: Methodsmentioning

confidence: 99%

Hydrogen Shift Reactions of Rhenium Hydrido Carbyne Complexes

et al. 2012

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“…Oil. 1 H NMR (400 MHz, CDCl 3 ) δ 8.10 (d, J = 8.9 Hz, 2H), 6.94 (d, J = 8.9 Hz, 2H), 3.88 (s, 3H), 2.48 (t, J = 7.1 Hz, 2H), 1.67 (m, 2H), 1.34-1.47 (m, 4H), 0.93 (t, J = 7.2 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 177.0, 164. 4 1-Thiophen-2-yl-oct-2-yn-1-one 3 Oil.…”

Section: -(4-methoxy-phenyl)-oct-2-yn-1onementioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 8.10 (d, J = 8.9 Hz, 2H), 6.94 (d, J = 8.9 Hz, 2H), 3.87 (s, 3H), 2.48 (t, J = 7.1 Hz, 2H), 2.19 (td, J = 6.8, 2. 6…”

Section: -Chloro-2-methyl-non-5-yn-4-onementioning

confidence: 99%

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A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides.

Wang¹,

Bonin²,

Micouin³

2005

ChemInform

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A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides. -Interestingly, starting from oxalyl chloride, the diynone (V) is formed instead of the corresponding diketo derivative. -(WANG, B.; BONIN, M.; MICOUIN*, L.; J. Org. Chem. 70 (2005) 15, 6126-6128; Lab. Chim. Ther., CNRS, Fac. Sci. Pharm. Biol., Univ. R. Descartes, F-75270 Paris, Fr.; Eng.) -Jannicke 49-053

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“…Reactions between enynylsilanes and acid chlorides require 1 equiv of titanium tetrachloride as Lewis acid, and only two examples have been reported . The cuprous-catalyzed reaction of acid chlorides and enynes can afford enynyl ketones in good yields in the presence of triethylamine as the base, but this method is not applicable to primary acid chlorides, such as acetyl, propanoyl, and butanoyl chlorides, which react readily with triethylamine PDC, or Swern reagents in moderate yields: the alcohols were prepared through the palladium-catalyzed coupling reactions between vinyl bromides and 3-hydroxyalkynylstannanes.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling Syntheses of Benzotriazolyl Enynes and a General Route to Enynyl Ketones and Alkynyl Ketones

Katritzky

Yao

1997

J. Org. Chem.

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A new general route to conjugated enynyl ketones was developed based on a two-step procedure. First, palladium-catalyzed cross-coupling reactions of 1-(benzotriazol-1-yl)propargyl ethyl ether (3) and vinyl triflates or vinyl bromides afforded the key intermediates [1-(benzotriazol-1-yl)-1-enynyl]methyl ethyl ethers 5a-d in good yields. Then reactions of compounds 5 with primary halides gave intermediates 8, which were hydrolyzed by dilute acid to enynyl ketones 9a-g. Similar palladium-catalyzed coupling reactions of 3 with various aryl iodides followed by an analogous sequence afforded aryl-substituted propargyl ethers 12a-d and thence alkynyl ketones 13a,b.

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A Facile Method of Synthesis of α-Acetylenic Ketones

Cited by 7 publications

References 5 publications

Hydrogen Shift Reactions of Rhenium Hydrido Carbyne Complexes

Hydrogen Shift Reactions of Rhenium Hydrido Carbyne Complexes

A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides.

Palladium-Catalyzed Cross-Coupling Syntheses of Benzotriazolyl Enynes and a General Route to Enynyl Ketones and Alkynyl Ketones

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