1854-56-4Relevant academic research and scientific papers
Nucleophilic and electrophilic double aroylation of chalcones with benzils promoted by the dimsyl anion as a route to all carbon tetrasubstituted olefins
Ragno, Daniele,Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Giovannini, Pier Paolo,Massi, Alessandro
, p. 1937 - 1945 (2015/02/19)
Dimsyl anion promoted the polarity reversal of benzils in a Stetter-like reaction with chalcones to give 2-benzoyl-1,4-diones (double aroylation products), which, in turn, were converted into the corresponding tetrasubstituted olefins via aerobic oxidative dehydrogenation catalyzed by Cu(OAc)2.
N-Heterocyclic carbene-catalyzed double acylation of enones with benzils
Takaki, Ken,Ohno, Akira,Hino, Makoto,Shitaoka, Takashi,Komeyama, Kimihiro,Yoshida, Hiroto
, p. 12285 - 12288 (2014/12/11)
Thiazolium carbene-catalyzed reaction of aromatic 1,2-diketones with enones in aprotic solvents gave double acylation products in good yields, whereas hydroacylation products formed by Stetter reaction were not detected at all. These results suggested the generation of aroyloxyenamine species from the 1,2-diketones instead of hydroxyenamines (Breslow intermediates). This journal is
The rearrangement of tert -butylperoxides for the construction of polysubstituted furans
Zheng, Xiaojian,Lu, Shenglin,Li, Zhiping
, p. 5432 - 5435 (2013/11/19)
The Bronsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstituted furans through a sequence of base-catalyzed Kornblum-DelaMare rearrangements and acid-promoted Paal-Knorr reactions.
Synthesis, X-ray Structure and Reactions of (2-Oxoalkyl)triarylbismuthonium Salts
Matano, Yoshihiro,Azuma, Nagao,Suzuki, Hitomi
, p. 1739 - 1748 (2007/10/02)
Treatment of triarylbismuth difluorides 1 with silyl enol ethers 2 in the presence of boron trifluoride-diethyl ether or trimethylsilyl trifluoromethanesulfonate (triflate) gave (2-oxoalkyl)triarylbismuthonium tetrafluoroborates 3 and triflates 4 in good yields.A similar reaction of the difluorides 1 with hexamethyldisiloxane in the presence of the latter acid reagent led to the formation of oxybis(triarylbismuth) ditriflates 5.X-Ray crystallographic analyses of compounds 3a, 4a and 5a showed that the first two onium salts have a distorted tetrahedral geometry and the last, a μ-oxo type compound, has a distorted trigonal bipyramidal geometry around the bismuth centre.The stability of these bismuthonium salts may reasonably be attributed to the intramolecular coordinative interaction between the bismuth and oxygen atoms and also low nucleophilicity of the counter ions employed.The bismuthonium salt 3f readily underwent onium exchange with the phosphine 6 and the sulfide 9 to afford the corresponding phosphonium and sulfonium salts 7 and 10.The salts 3 and 4 also underwent coupling with a variety of nucleophiles such as the enolate 11, piperidine 13, the phenoxides 15, the thiolates 17, the sulfinate 19 and the halides 21 to afford the corresponding α-substituted ketones 12, 14, 16, 18, 20 and 22 in moderate to good yields, together with a good recovery of triphenylbismuthine 8.
A Novel Synthesis of Alkylbismuthonium Salts and their Reaction with Some Nucleophiles. First X-Ray Structural Analysis of a Stabilized Alkylbismuthonium Tetrafluoroborate
Matano, Yoshihiro,Azuma, Nagao,Suzuki, Hitomi
, p. 8457 - 8460 (2007/10/02)
Treatment of triarylbismuth difluorides 1 with silyl enol ethers 2 in the presence of BF3*OEt2 gives (2-oxoalkyl)triarylbismuthonium tetrafluoroborates 3 as a stable crystalline solid, the bismuth centre of which has been found by X-ray analysis to posses
