Aromatic nucleophilic substitution with sulphoxides: The interaction of dimethyl sulphoxide with chloronitrobenzenes

1974 ◽  
Vol 27 (4) ◽  
pp. 777 ◽  
Author(s):  
MEC Biffin ◽  
DB Paul
Keyword(s):  
Nucleophilic Substitution ◽  
Benzyl Alcohol ◽  
Sodium Benzoate ◽  
Sodium Acetate ◽  
Dimethyl Sulphoxide ◽  
Substituted Phenols ◽  
Aromatic Nucleophilic Substitution ◽  
Decomposition Products ◽  
Chlorine Atoms ◽  
Kornblum Oxidation

Activated chlorine atoms are displaced by sulphoxide oxygen when di- and tri-nitrochlorobenzenes are heated in dimethyl sulphoxide. The corresponding phenols, thiomethoxymethyl- and formyl- substituted phenols, thioanisoles and decomposition products of chlorodimethyl sulphide are formed. Monochloronitrobenzenes do not undergo reaction with Me2SO even at 190�, but in the presence of added sodium acetate or sodium benzoate, phenols and thioanisoles are obtained together with products derived from the sulphonium ylid CH3S+=CH2. These observations are rationalized mechanistically. The reaction mixtures are shown to oxidize benzyl alcohol to benzaldehyde. These results do not substantiate the presence of an intermediate sulphonium complex, however, because benzyl alcohol competes more favourably for the chloroaromatic system than does Me2SO; benzyl alcohol forms the chloride which then undergoes a Kornblum oxidation to yield benzaldehyde.

The preparation of 3-amino-3-deoxy-1,2-O-isopropylidene-α-L-erythrofuranose, 3-amino-3-deoxy-1,2-O-isopropylidene-β-D-threofuranose and their derivatives

1980 ◽  
Vol 45 (12) ◽  
pp. 3378-3390 ◽  
Author(s):  
Jiří Jarý ◽  
Milena Masojídková ◽  
Ivan Kozák ◽  
Miroslav Marek ◽  
Jan Staněk
Keyword(s):  
Nucleophilic Substitution ◽  
Sodium Azide ◽  
Sodium Benzoate ◽  
Nmr Spectra ◽  
Subsequent Reduction ◽  
H Nmr ◽  
Amino Derivatives

The title amino derivatives VI and XIV were prepared by nucleophilic substitution of p-toluenesulfonyl derivatives II and XVII with sodium azide or hydrazine and subsequent reduction. Nucleophilic substitution of compounds II and XVII with sodium benzoate was also investigated. The 1H NMR spectra of the substances prepared are discussed.

scholarly journals EFFECT OF COCAINE ON THE GROWTH OF LUPINUS ALBUS. A CONTRIBUTION TO THE COMPARATIVE PHARMACOLOGY OF ANIMAL AND PLANT PROTOPLASM

1922 ◽  
Vol 4 (5) ◽  
pp. 573-584 ◽  
Author(s):  
David I. Macht ◽  
Marguerite B. Livingston
Keyword(s):  
Sodium Benzoate ◽  
Lupinus Albus ◽  
The Other ◽  
Plant Roots ◽  
Animal Tissues ◽  
Decomposition Products ◽  
Other Hand ◽  
Low Toxicity

1. The effects of cocaine and its decomposition products were studied on the growth of the young roots of Lupinus albus. 2. The results obtained were compared with similar experiments on animal tissues. 3. It was found that, while cocaine is the most toxic of these compounds studied for animal tissues, it was of comparatively low toxicity in respect to its effect on the growth of roots. On the other hand, sodium benzoate, being practically non-toxic for animals, was the most toxic of the compounds studied for the plant roots.

Phosphonium salts. III. The action of cyanide ion and other nucleophiles on some bis-phosphonium salts

1969 ◽  
Vol 22 (7) ◽  
pp. 1405 ◽  
Author(s):  
JJ Brophy ◽  
MJ Gallagher
Keyword(s):  
Sodium Azide ◽  
Sodium Methoxide ◽  
Sodium Acetate ◽  
Potassium Cyanide ◽  
Dimethyl Sulphoxide ◽  
High Yield ◽  
Phosphonium Salts ◽  
Elimination Reaction ◽  
Cyanide Ion ◽  
Reaction Proceeds

Cyclic and acyclic bis-phosphonium salts with a two-carbon bridge are smoothly cleaved to phosphines in high yield by potassium cyanide in dimethyl sulphoxide. Evidence is presented that the reaction proceeds by an elimination-addition sequence. An elimination reaction also occurs when sodium methoxide, sodium azide, sodium acetate, and triethylamine react with ethane-1,2-bis(tri-phenylphosphonium) dibromide. ��� In a novel reaction, triphenylphosphine is converted into its oxide by a mixture of sodium azide and dimethyl sulphoxide.

Sign in / Sign up

Export Citation Format

Share Document