scholarly journals Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides

2015 ◽  
Vol 11 ◽  
pp. 242-248 ◽  
Author(s):  
Akihiro Shimizu ◽  
Ryutaro Hayashi ◽  
Yosuke Ashikari ◽  
Toshiki Nokami ◽  
Jun-ichi Yoshida
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Hydroxide ◽  
Sodium Methoxide ◽  
Reaction Pathways ◽  
Halocarbonyl Compounds

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br+ and I+ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

Acridone studies. XIV. The selective demethylation of 2,3-Dimethoxy-10-methyl-9-oxoacridine-1,4-quinone by base

1975 ◽  
Vol 28 (6) ◽  
pp. 1351 ◽  
Author(s):  
JR Cowan ◽  
DKC Hodgeman ◽  
RH Prager
Keyword(s):  
Sodium Hydroxide ◽  
Sodium Methoxide ◽  
Reaction Pathways ◽  
Methoxyl Group ◽  
Product Composition ◽  
Relative Extent ◽  
Kinetics Of

The selective demethylation of 2,3-dimethoxy-10-methyl-9-oxoacridine- 1,4-quinone by sodium hydroxide has been studied by following the change in product composition with hydroxide concentration, by measuring the relative extent of exchange at C2 and C3 with sodium methoxide[T], and by following the kinetics of the reaction in alkali. Reaction pathways are proposed to rationalize the observation that the C2 methoxyl group is replaced more readily in dilute alkali or on warming, but the C 3 methoxyl group is replaced in more concentrated alkali.

Regioselective Alkylation of β-Cyclodextrin

1998 ◽  
Vol 51 (10) ◽  
pp. 915 ◽  
Author(s):  
Paramjit S. Bansal ◽  
Craig L. Francis ◽  
Noel K. Hart ◽  
Scott A. Henderson ◽  
David Oakenfull ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Dimethyl Sulfoxide ◽  
Sodium Hydroxide ◽  
Alkyl Halides ◽  
Barium Hydroxide ◽  
Analytical Methodology ◽  
Regioselective Alkylation ◽  
Benzyl Ethers ◽  
Hydroxy Groups

Methodology for preparation of heptakis(2,6-di-O-alkyl)-β-cyclodextrins, heptakis(2-O-alkyl)-β- cyclodextrins, and heptakis(6-O-alkyl)-β-cyclodextrins in substantially purified form has been developed. Treatment of β-cyclodextrin (1) with sodium or barium hydroxide and various alkyl halides in dimethyl sulfoxide or a mixture of dimethyl sulfoxide and N,N-dimethylformamide provided the corresponding heptakis(2,6-di-O-alkyl)-β-cyclodextrins. Treatment of heptakis(6-O-t-butyldimethylsilyl)-β-cyclodextrin (5) with sodium hydroxide and several haloalkanes in dimethyl sulfoxide followed by desilylation provided heptakis(2-O-alkyl)-β-cyclodextrins. Protection of the secondary hydroxy groups of the t-butyldimethylsilyl-β-cyclodextrin (5) as benzyl ethers, followed by desilylation, alkylation, and debenzylation afforded several heptakis(6-O-alkyl)-β-cyclodextrins. Analytical methodology has been developed to characterize all of these compounds, with the homogeneity of the pattern of substitution verified by h.p.l.c. analysis, f.a.b.–mass spectrometry and n.m.r. spectroscopy.

scholarly journals Cleavage of the methylenedioxy group with sodium methoxide in dimethyl sulfoxide.

1978 ◽  
Vol 26 (10) ◽  
pp. 3113-3116 ◽  
Author(s):  
SHIGERU KOBAYASHI ◽  
MASARU KIHARA ◽  
YOSHINOBU YAMAHARA
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Methoxide ◽  
Methylenedioxy Group

ChemInform Abstract: DEHALOGENATION OF 1-HALOTHIENYLDI- AND -TETRAHYDROISOQUINOLINES BY SODIUM METHOXIDE IN DIMETHYL SULFOXIDE

1985 ◽  
Vol 16 (23) ◽  
Author(s):  
J. M. BARKER ◽  
P. R. HUDDLESTON ◽  
J. CLEPHANE ◽  
M. L. WOOD ◽  
D. HOLMES
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Methoxide
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