Substituent effects of positive poles in aromatic substitution. Part VII. Effect of nitrogen and arsenic poles on the orientation and rate of bromination by hypobromous acid

1969 ◽  
pp. 684
Author(s):  
Alicia Gastaminza ◽  
J. H. Ridd ◽  
Falmai Roy
Keyword(s):  
Substituent Effects ◽  
Aromatic Substitution ◽  
Hypobromous Acid

Substituent Effects of Phosphorus and Arsenic Containing Groups in Aromatic Substitution. IV. Nitration of Aromatic Phosphine Oxides

1975 ◽  
Vol 53 (10) ◽  
pp. 1468-1474 ◽  
Author(s):  
Edmund Malinski ◽  
Antonina Piekos ◽  
Tomasz A. Modro
Keyword(s):  
Sulfuric Acid ◽  
Benzene Ring ◽  
Phosphorus Atom ◽  
Substituent Effects ◽  
Ortho Position ◽  
Phosphine Oxides ◽  
Aromatic Substitution ◽  
Tertiary Phosphine ◽  
Aqueous Sulfuric Acid

The nitration of some tertiary phosphine oxides ArP(O)R2 in aqueous sulfuric acid has been investigated. All compounds studied react as conjugate acids. When the phosphinyl group is bonded directly to the benzene ring, high deactivation and meta-orientation is found, accompanied in most cases by some substitution at the ortho position. The substituent effects of the "quasiphosphonium" group P(OH)R2+are compared with those of structurally related systems and are discussed in terms of pπ–dπ, interactions of the oxygen and the phosphorus atom.

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