ChemInform Abstract: N-Alkylations of NH-Sulfoximines and NH-Sulfondiimines with Alkyl Halides Mediated by Potassium Hydroxide in Dimethyl Sulfoxide.

ChemInform ◽  
2014 ◽  
Vol 45 (45) ◽  
pp. no-no
Author(s):  
Christine M. M. Hendriks ◽  
Rebekka A. Bohmann ◽  
Marina Bohlem ◽  
Carsten Bolm
Keyword(s):  
Dimethyl Sulfoxide ◽  
Potassium Hydroxide ◽  
Alkyl Halides

Synthesis of Simple Unsymmetrical Ethers from Alcohols and Alkyl Halides or Sulfates: The Potassium Hydroxide/Dimethyl Sulfoxide System

Synthesis ◽  
1979 ◽  
Vol 1979 (06) ◽  
pp. 428-429 ◽  
Author(s):  
David R. Benedict ◽  
Thomas A. Bianchi ◽  
Laurence A. Cate
Keyword(s):  
Dimethyl Sulfoxide ◽  
Potassium Hydroxide ◽  
Alkyl Halides

N-Alkylations ofNH-Sulfoximines andNH-Sulfondiimines with Alkyl Halides Mediated by Potassium Hydroxide in Dimethyl Sulfoxide

2014 ◽  
Vol 356 (8) ◽  
pp. 1847-1852 ◽  
Author(s):  
Christine M. M. Hendriks ◽  
Rebekka A. Bohmann ◽  
Marina Bohlem ◽  
Carsten Bolm
Keyword(s):  
Dimethyl Sulfoxide ◽  
Potassium Hydroxide ◽  
Alkyl Halides

scholarly journals Aliphatic diazo compounds. IX. The base-induced dimerization of α-diazo ketones

1969 ◽  
Vol 47 (21) ◽  
pp. 3997-4004 ◽  
Author(s):  
Peter Yates ◽  
R. G. F. Giles ◽  
D. G. Farnum
Keyword(s):  
Benzoic Acid ◽  
Dimethyl Sulfoxide ◽  
Potassium Hydroxide ◽  
Ammonium Acetate ◽  
Butyl Alcohol ◽  
Diazo Compounds ◽  
Prolonged Treatment ◽  
Independent Synthesis

Treatment of 2-diazoacetophenone (1) with potassium t-butoxide in t-butyl alcohol gives a colorless dimer, which is shown to be 5-benzoyl-2-phenacyltetrazole (4) by its independent synthesis by phenacylation of 5-benzoyltetrazole. The latter reaction also gives 5-benzoyl-1-phenacyltetrazole (3), which is distinguished from 4 by its reduction to di(2-hydroxy-2-phenylethyl)amine and by its cyclization on treatment with ammonium acetate. The assignment of the structure of the colorless dimer of 1 permits the postulation of related pathways for its formation and that of the red-brown dimer obtained on treatment of 1 with potassium hydroxide in dimethyl sulfoxide. 2-Phenacyltetrazole (22) and benzoic acid are formed in addition to 4 on treatment of 1 with potassium t-butoxide in t-butyl alcohol; these are considered to arise via cleavage of 4, since prolonged treatment of 4 and 3 with potassium t-butoxide in t-butyl alcohol gives 22 and 1-phenacyltetrazole (24), respectively. Compounds 22 and 24 have been prepared independently by phenacylation of tetrazole.

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.

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