75437-87-5Relevant academic research and scientific papers
Regioselective cleavage reaction of the aromatic methylenedioxy ring. V. Cleavage with sodium alkoxides-alcohols, potassium tert-butoxide-alcohols, dimsyl anion-methyl alcohol, metallic sodium-alcohols, and sodium cyanide in dipolra aprotic solvents
Imakura,Okimoto,Konishi,Hisazumi,Yamazaki,Kobayashi,Yamashita
, p. 1691 - 1696 (2007/10/02)
The reaction of aromatic methylenedioxy compounds containing electron-withdrawing groups with dimsyl anion-methyl alcohol, potassium tert-butoxide-alcohols, and metallic sodium-alcohols in dimethyl sulfoxide (DMSO), and with sodium alkoxides-alcohols in hexamethylphosphoramide, gave 3- and 4-hydroxybenzene derivatives in good yield by regioselective attack of the alkoxide ions on the methylenedioxy ring. The formation mechanism of alkoxide ions and the effect of DMSO in the cleavage reaction of the methylenedioxy ring are discussed on the basis of proton nuclear magnetic resonance (1H-NMR) spectra. The reactions of aromatic methylenedioxy compounds (3 and 22) with sodium cyanide in dipolar aprotic solvents gave 4-cyano-3-hydroxybenzene derivatives (23 and 24) by regioselective attack of the cyanide ion on the methylenedioxy ring. The reactions of aromatic methylenedioxy compounds (28-30) containing no electron-withdrawing group with MeONa-MeOH in dipolar aprotic solvents gave non-regioselective cleavage products (31 and 34).
REGIOSELECTIVE CLEAVAGE REACTION OF THE METHYLENEDIOXY RING IN AROMATIC COMPOUNDS CONTAINING ELECTRONWITHDRAWING GROUPS WITH SODIUM ALKOXIDES-ALCOHOLS IN DIMETHYL SULFOXIDE
Imakura, Yasuhiro,Okimoto, Kazuto,Gorohata, Chizuru,Kobayashi, Shigeru,Kihara, Masaru,Yamashita, Shinsuke
, p. 1067 - 1076 (2007/10/02)
The reaction of 6-bromopiperonal (1) with sodium alkoxides (MeONa or PhCH2ONa)-alcohols (MeOH or PhCH2OH), and sodium alkoxides (MeONa, PhCH2ONa or PhONa)-phenol (PhOH) in dimethyl sulfoxide gave 3-hydroxybenzene derivatives (3, 5 and 6) and 4-hydroxybenzene derivative (4), respectively.The reactivity and formational mechanism of various nucleophilic reagents (alkoxide anions) formed from the alcohols and phenol by sodium alkoxides in the regioselective cleavage reactions are discussed.
Cleavage of Methylenedioxy Ring. II. Cleavage with Sodium Phenoxide and Methoxide in Dimethyl Sulfoxide
Kobayashi, Shigeru,Imakura, Yasuhiro,Horikawa, Ritsuko
, p. 1287 - 1293 (2007/10/02)
Regioselective cleavage of the methylenedioxy ring in piperonals (1, 6, and 7) and 3,4-methylenedioxynitrobenzenes (8 and 9) by oxide ions in dimethyl sulfoxide was achieved: the 4-hydroxybenzene derivatives (2, 10-13, and 22) were obtained with the phenoxide ion, while the 3-hydroxybenzene derivatives (4, 18-21, 23, 26, and 29) were obtained with the methoxide or benzyloxide ion.Keywords - cleavage of methylenedioxy ring; regioselectivity; piperonals; 3,4-methylenedioxynitrobenzenes; sodium phenoxide; sodium methoxide; dimethyl sulfoxide; 3-hydroxybenzene derivatives; 4-hydroxybenzene derivatives; NMR spectra
