Oxidative Cyclizations. V. The Oxidation of ortho-Substituted Benzenamines with Lead(IV) Tetraacetate

1979 ◽  
Vol 32 (3) ◽  
pp. 643 ◽  
Author(s):  
LK Dyall
Keyword(s):  
Experimental Evidence ◽  
Base Pair ◽  
Reactive Intermediates ◽  
Oxidative Cyclization ◽  
Azo Compounds ◽  
Acid Base ◽  
Oxidative Cyclizations ◽  
Conjugate Acid

Lead(IV) tetraacetate has been used to oxidize 1-aminoanthraquinone, 1-arylazonaphthalen-2-amines and benzenamines whose ortho-substitutents were arylazo, nitro, or benzopl. Only the amines with ortho-arylazo substituents underwent oxidative cyclization, to yield triazoles; the others yielded azo compounds and polymers. Experimental evidence shows that neither nitrenes nor arenamino ('anilenium') cations can be the reactive intermediates in some of these reactions. All the results can be rationalized in terms of the conjugate acid-base pair of intermediates, arenamine cation ArNH2+' and arenamino ArNH.

Design and synthesis of solid state structures with conjugate acid–base pair interactions

CrystEngComm ◽  
2012 ◽  
Vol 14 (11) ◽  
pp. 3851 ◽  
Author(s):  
Sathyanarayana Reddy Perumalla ◽  
Changquan Calvin Sun
Keyword(s):  
Solid State ◽  
Base Pair ◽  
Acid Base ◽  
Design And Synthesis ◽  
Conjugate Acid ◽  
Solid State Structures ◽  
Pair Interactions

Stabilization of tyrosine-O-sulfate residues through the formation of a conjugate acid-base pair

2006 ◽  
pp. 370-372
Author(s):  
T. Yagami ◽  
K. Kitagawa ◽  
C. Aida ◽  
H. Fujiwara ◽  
S. Futaki
Keyword(s):  
Base Pair ◽  
Acid Base ◽  
Conjugate Acid

scholarly journals An ultra-stable oxoiron(iv) complex and its blue conjugate base

2014 ◽  
Vol 5 (3) ◽  
pp. 1204-1215 ◽  
Author(s):  
Jason England ◽  
Jennifer O. Bigelow ◽  
Katherine M. Van Heuvelen ◽  
Erik R. Farquhar ◽  
Marléne Martinho ◽  
...  
Keyword(s):  
Base Pair ◽  
Carbonyl Oxygen ◽  
Acid Base ◽  
Conjugate Acid ◽  
Conjugate Base

We report the first conjugate acid–base pair of nonheme oxoiron(iv) complexes, which are supported by a tetramethylcyclam ligand with a pendant amide that binds trans to the oxo group via the carbonyl oxygen.

Stabilization of a tyrosine O -sulfate residue by a cationic functional group: formation of a conjugate acid-base pair

2000 ◽  
Vol 56 (4) ◽  
pp. 239-249 ◽  
Author(s):  
T. Yagami ◽  
K. Kitagawa ◽  
C. Aida ◽  
H. Fujiwara ◽  
S. Futaki
Keyword(s):  
Base Pair ◽  
Functional Group ◽  
Group Formation ◽  
Acid Base ◽  
Conjugate Acid

Oxidative cyclizations. VII. Cyclization of 2-substituted anilines with alkaline hypohalite

1984 ◽  
Vol 37 (10) ◽  
pp. 2013 ◽  
Author(s):  
LK Dyall
Keyword(s):  
Oxidative Cyclization ◽  
Azo Compounds ◽  
Substituted Anilines ◽  
Oxidative Cyclizations ◽  
Visible Spectra ◽  
Transient Intermediates ◽  
Ortho Substituent

The Green-Rowe oxidation of 2-nitroanilines with alkaline hypochlorite, to yield benzofuroxans, is demonstrated by studies of the visible spectra of transient intermediates to proceed through N-chlorination and a singlet nitrene. Two variations on the route to the nitrene are possible. The cyclization step is represented as an internal capture of the nitrene by the ortho substituent, and on this basis the Green-Rowe oxidative cyclization is now extended to anilines whose ortho substituent is benzoyl or phenylazo. It is not however successful for ortho phenyl. Azo compounds were observed as byproducts in some of these reactions, and are shown to arise via N,N-dichloroanilines.

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