20294-39-7Relevant articles and documents
Molecular complexity from aromatics: A novel, stereoselective route to tricyclo[5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6] dodecenones, and [n.3.3]propellanes
Singh, Vishwakarma,Sahu, Pramod K.,Singh, Raj Bahadur,Mobin, Shaikh M.
, p. 10155 - 10165 (2007)
(Chemical Equation Presented) A general stereoselective route to functionalized and substituted tricyclo [5.2.2.01,5]undecenones, tricyclo-[6.2.2.01,6]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo-[5.2.2.01,5]undecenones and tricyclo[6.2.2.01,6]dodecenones endowed with a β,γ-enone chromophore. Photochemical reaction of the tricyclic chromophoric systems followed by reductive cleavage provided an efficient entry into propellanes.
Gold catalysis: Domino reaction of En-diynes to highly substituted phenols
Hashmi, A. Stephen K.,Haeffner, Tobias,Rudolph, Matthias,Rominger, Frank
supporting information; experimental part, p. 8195 - 8201 (2011/09/12)
By Sonogashira coupling of 1,7-heptadiynes and 1,8-octadiynes with 2-iodoallyl alcohols, various substrates that bear a 2-alkynylallyl alcohol moiety tethered to an additional alkyne were prepared in one step. Subjection to nitrogen acyclic carbene (NAC)/gold(I) catalysts delivered highly substituted phenols in an efficient domino reaction. Furan derivatives were formed as intermediates; this was proven by in situ NMR spectroscopy. The uncommon substitution pattern of these furans opens the way for a selective formation of phenols that contain the hydroxyl group in the meta position to the ring junction, which previously was not possible by gold-catalyzed furan-yne cyclization. Furthermore, interesting mechanistic insights were obtained by products derived from secondary allyl alcohols. In this case, in addition to the phenolic compounds, a ketone is formed by 1,2-alkyl shift.
Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne - Ketenes
Tarli, Anna,Wang, Kung K.
, p. 8841 - 8847 (2007/10/03)
Enediynyl ethyl ethers 14/17 were synthesized by using the Pd(PPh3)4-catalyzed cross-coupling factions between enynyl iodides 13/16 and (2-ethoxyethynyl)zinc chloride. Thermolysis of these enediynyl ethyl ethers in refluxing chlorobenzene (132°C) promoted a retro-ene reaction to produce enyne - ketenes, which underwent the Moore cyclization reactions to form the biradicals having a phenyl radical center and a phenoxy radical center. The presence of two radical centers in he same molecule simultaneously provided many opportunities for intramolecular decay through disproportionate, radical - radical combination, and the formation of o-quinone methide.
Alkylations of Tetracarbonyl(phosphine)chromium and Pentacarbonylchromium Carbene Complexes and Their Reactions with Selected Acetylenes
Xu, Yao-Chang,Wulff, William D.
, p. 3263 - 3275 (2007/10/02)
The thermodynamic acidity of (methylmethoxymethylene)tetracarbonyl(tri-n-butylphosphine)chromium (1b) was found to be 6 orders of magnitude less than that of (methylmethoxymethylene)pentacarbonylchromium (1a).The anion 2b is generated from 1b by deprotona
SYNTHESIS OF PHENOLS FROM METAL-CARBYNES AND DIYNES
Sivavec, Timothy M.,Katz, Thomas J.
, p. 2159 - 2162 (2007/10/02)
Metal-carbynes RCM(CO)4Br with diacetylenes give specific phenols in good yield.The reactions take only a few minutes at or below room temperature.
Synthesis and antianxiety activity of (ω-piperazinylalkoxy)indan derivatives
Kikumoto,Tobe,Fukami,Egawa
, p. 246 - 250 (2007/10/02)
A series of (ω-piperazinylalkoxyl)indan derivatives has been synthesized and screened for potential antianxiety activities. The effect of structural modification of these molecules on activities has been systematically examined. Antianxiety activity was displayed by 5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (2), 5-[3-(4-[4-fluorophenyl)-1-piperazinyl]propoxy]indan (8), 6-fluoro-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (33), and 6-methyl-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (42), as determined in antifighting and anti-morphine tests. These derivatives in antianxiety tests were equipotent or more potent than chloridazepoxide with less muscle-relaxant effect. They also showed weak neuroleptic-like action.