32454-12-9Relevant articles and documents
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.
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.
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.