32454-12-9Relevant academic research and scientific papers
A convenient ring formation of 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans from phenols and 2-aryl-2,2-dialkylacetaldehydes
Yamashita, Makoto,Ono, Yujirou,Tawada, Hiroyuki
, p. 2843 - 2849 (2004)
A new and simple route for the preparation of 3-aryl-2,2-dialkyl-2,3- dihydrobenzofurans from phenols is described. In the presence of an acid catalyst phenols react with 2-aryl-2,2-dialkylacetaldehydes, prepared in good yield from 2-arylacetonitriles in 2 steps, to give 3-aryl-2,2-dialkyl-2,3- dihydrobenzofurans. Electron-donating substituents were required on the phenols in order to give 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans in good yield.
CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes
Wang, Zhihui,Li, Meiyi,Zhang, Wenqin,Jia, Jiangnan,Wang, Fei,Xue, Song
supporting information; experimental part, p. 5968 - 5971 (2011/11/29)
A highly efficient and selective rearrangement reaction of bromohydrins to aldehydes mediated by CF3CO2ZnEt was described. The secondary and tertiary aldehydes were prepared under mild conditions in good to excellent yields (85-99%). The scope and limitations of this rearrangement process were also investigated.
GaCl3-catalyzed skeletal rearrangement of α,α, α-trisubstituted aldehydes
Oshita, Masayuki,Okazaki, Takao,Ohe, Kouichi,Chatani, Naoto
, p. 331 - 334 (2007/10/03)
(Chemical Equation Presented) GaCl3 is found to be a superior catalyst for the skeletal rearrangement of α,α,α- trisubstituted aldehydes to ketones. The rearrangement can proceed smoothly in the presence of a catalytic amount of GaCl3, and even substrates having no heteroatoms α to the carbonyl group or without steric strains can be used. Double activation of a carbonyl group by two molecules of GaCl 3 was supported on the basis of experimental data and a DFT study.
Arylation of allylic alcohols in ionic liquids catalysed by a Pd-benzothiazole carbene complex
Calo, Vincenzo,Nacci, Angelo,Monopoli, Antonio,Spinelli, Michele
, p. 1382 - 1385 (2007/10/03)
The reaction of aryl bromides with allylic alcohols catalysed by a Pd-benzothiazole carbene complex, in tetrabutylammonium bromide as solvent, leads principally to β-arylated carbonyl compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Reactions of a β-sultam ring with Lewis acids via the C-S bond cleavage
Iwama, Tetsuo,Ogawa, Miyoko,Kataoka, Tadashi,Muraoka, Osamu,Tanabe, Genzoh
, p. 8941 - 8974 (2007/10/03)
Selective C-S bond cleavage of a β-sultam ring was achieved by the reactions with Lewis acids. Aryl ketones or aldehyde were provided from 3- aryl-β-sultams whereas β-sultams bearing a poorly migratory substituent at C-3 gave trans-1,2,3-oxathiazolidine 2-oxides and/or cis-aziridines. These reactions were influenced by the cation-stabilizing capability of C-4 substituents and by the configuration of the substituents at C-3 and C-4. Some 4-alkenyl-3-aryl-β-sultams underwent tandem intramolecular cyclization to give bicyclo[3.2.1]- and [2.2.1]-γ-sultams via the processes of C-S bond cleavage, 1,2-aryl shift, cation-olefin cyclization and recombination of the sulfonyl anion.
Selective C-S bond cleavage of 3-aryl-β-sultams with EtAlCl2
Kataoka,Iwama
, p. 245 - 248 (2007/10/02)
Selective C-S bond cleavage of β-sultam ring was achieved by the reactions of 3-aryl-β-sultams 1 with EtAlCl2. Aryl ketones 2 or aldehyde 3 were provided via processes of the C-S bond cleavage, 1,2-aryl shift and imine formation. These reactions were influenced by the cation stabilizing capability of C-4 substituents and by the configuration of the substituents at C-3 and C-4.
Α-ARYLATION OF ALDEHYDES VIA Α-CHLOROALDIMINES
Kimpe, Norbert De,Zi-Peng, Yao,Schamp, Niceas
, p. 481 - 496 (2007/10/02)
α-Chloroaldimines are arylated at the α-position under Friedel-Crafts conditions via the presumptive intermediacy of α-imidoylcarbenium ions.Aluminium (III)chloride in arenes cleanly converted α-chloro-α-phenylaldimines into α-aryl-α-phenylaldimines.Aliphatic α-chloroaldimines could only be converted into the corresponding α-arylaldimines in low to moderate yields due to a lower reactivity and a competitive side reaction, i.e. dehydrochlorination into 1-aza-1,3-dienes. α-Bromo- and α-iodoaldimines were also evaluated under the given Friedel-Crafts conditions but the results appeared to be negative.The formation of all reaction products (i.e. α-arylaldimines, 1-aza-1,3-dienes and indolines) from the reaction of α-chloroaldimines with arenes in the presence of Lewis acids could be explained by the intermediacy of α-imidoylcarbenium ions, the chemistry of which is discussed to some extent.
FRIEDEL-CRAFTS REACTION OF α-CHLOROALDIMINES : POSSIBLE INTERMEDIACY OF α-IMIDOYLCARBENIUM IONS
Kimpe, Norbert De,Verhe, Roland,Buyck, Laurent De,Schamp, Niceas,Charpentier-Morize, Micheline
, p. 2853 - 2856 (2007/10/02)
α-Chloroaldimines are arylated at the α-position under Friedel-Crafts conditions via intermediacy of α-imidoylcarbenium ions.
