15994-22-6Relevant academic research and scientific papers
Dehydration of Alcohols Catalysed by Heteropolyacids Supported on Silica
Alesso, Elba,Torviso, Rosario,Finkielsztein, Liliana,Lantano, Beatriz,Moltrasio, Graciela,Aguirre, Jose,Vazquez, Patricia,Pizzio, Luis,Caceres, Carmen,Blanco, Mirta,Thomas, Horacio
, p. 1232 - 1245 (2007/10/03)
Keggin type heteropolyacids supported on silica efficiently dehydrate secondary and tertiary alcohols under mild conditions and in good yields to afford the correspondent alkenes.
Acid reactions of the lignin model 1,2-Bis(3,4-dimethoxyphenyl)-1,3-propanediol
Li, Shiming,Karlsson, Olov,Lundquist, Knut,Stomberg, Rolf
, p. 431 - 437 (2007/10/03)
1,2-Bis(3,4-dimethoxyphenyl)-1,3-propanediol on acid treatment [refluxing with 0.1 M (or 0.2 M) acid in dioxane-water (9:1)] undergoes two competing reactions: a reverse Prins reaction leading to (E)-3,3′,4,4′-tetramethoxystilbene (and formaldehyde) and a dehydration with formation of aryl-substituted allyl alcohols [the E and Z forms of 2,3-bis(3,4-dimethoxyphenyl)-2-propen-1-ol, 1,2-bis(3,4-dimethoxyphenyl)-2-propen-1-ol] that are comparatively slowly converted into a series of carbonyl compounds [1,2-bis(3,4-dimethoxyphenyl)-1-propanone, 2,2-bis(3,4-dimethoxyphenyl)propanal, 1,1-bis(3,4-dimethoxyphenyl)-2-propanone, 2,3-bis(3,4-dimethoxyphenyl)propanal] and 2-(3,4-dimethoxyphenyl)-5,6-dimethoxy-1H-indene. HBr (and to a lesser extent HCl) catalyses the formation of allyl alcohols while only traces of these compounds are formed when CH3SO3H is used as the catalyst [(.E)-3,3′,4,4′-tetramethoxystilbene is the predominant reaction product]. HBr promotes the formation of 1,2-bis(3,4-dimethoxyphenyl)-1-propanone from the intermediate (E)-2,3-bis(3,4-dimethoxyphenyl)-2-propen-1-ol. α-Chloromethyl-3,3′,4,4′-tetramethoxystilbene and α-bromomethyl-3,3′,4,4′-tetramethoxystilbene are formed in the reactions catalysed by HCl and HBr, respectively. The preparation and/or isolation of most of the detected acidolysis products is described and their stereochemistry is elucidated. A stereoselective synthesis of threo-1,2-bis(3,4-dimethoxyphenyl)-1,3-propanediol involving hydroboration-oxidation of (E)-2,3-bis(3,4-dimetnoxyphenyl)propenoic acid is reported. Acta Chemica Scandinavica 1997.
Synthesis and nuclear magnetic resonance spectroscopy of indane structures: indanes mono- and disubstituted in the pentagonal ring
Alesso, Elba N.,Tombari, Dora G.,Ibanez, Adriana F.,Iglesias, Graciela Y. Moltrasio
, p. 1166 - 1170 (2007/10/02)
Indanes monosubstituted and 1,2- and 1,3-disubstituted in the pentagonal ring were synthesized, and configurations were assigned to the 1,2-disubstituted compounds by means of nuclear magnetic resonance spectroscopy.Key words: mono- and disubstituted indanes, conformation, configuration, 1H and 13C NMR, synthesis.
