Acylations of Nitriles with Esters by Sodium Amide in Liquid Ammonia to Form β-Ketonitriles. Consideration of Amidine Formation1

1957 ◽  
Vol 79 (3) ◽  
pp. 723-725 ◽  
Author(s):  
Charles J. Eby ◽  
Charles R. Hauser
Keyword(s):  
Liquid Ammonia ◽  
Sodium Amide

Study of the reaction of sodium amide in liquid ammonia with hexahydro-(1h)-2-benzazoninium salts : access to 2-aza-(7)-metacyclophanes

Tetrahedron ◽  
1991 ◽  
Vol 47 (1) ◽  
pp. 47-52 ◽  
Author(s):  
Didier Barbry ◽  
Damien Spanneut ◽  
Bruno Hasiak ◽  
Daniel Couturier
Keyword(s):  
Liquid Ammonia ◽  
Sodium Amide

The Reaction of Dihaloanisoles with Sodium Amide in Liquid Ammonia

1953 ◽  
Vol 75 (13) ◽  
pp. 3196-3197 ◽  
Author(s):  
Robert A. Benkeser ◽  
Gene Schroll
Keyword(s):  
Liquid Ammonia ◽  
Sodium Amide

Organophosphorus compounds. VI. The 'abnormal' Michaelis-Becker reaction. Diethyl 1-phenylepoxyethylphosphonate and diethyl 1-phenylvinylphosphate from diethyl phosphonate and phenacyl chloride

1965 ◽  
Vol 18 (2) ◽  
pp. 168 ◽  
Author(s):  
A Meisters ◽  
JM Swan
Keyword(s):  
Sodium Hydroxide ◽  
Hydrogen Chloride ◽  
Liquid Ammonia ◽  
Organophosphorus Compounds ◽  
Ammonia Solution ◽  
Sodium Amide

Phenacyl chloride reacts with sodium diethyl phosphonate in liquid ammonia solution to yield a 7 : 3 mixture of diethyl 1-phenylepoxyethylphosphonate (Ia) and the isomeric diethyl 1-phenylvinyl phosphate (IIa). Reaction of phenacyl chloride with diethyl phosphonate and triethylamine in benzene gives only diethyl 1-phenylvinyl phosphate. The action of hydrogen chloride on the epoxide (Ia) gives diethyl 2-chloro-1-hydroxy-1-phenylethylphosphonate (IV). This chlorohydrin reacts with sodium amide in liquid ammonia or with sodium hydroxide in ethanol to again yield a mixture of (Ia) end (IIa); with triethylamine in benzene, the product is mainly the vinyl phosphate (IIa).

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