The DNP-derivatives of diphenylcyclopropenone 4-azatriafulvenes

E. D. Bergmann; I. Agranat

doi:10.1016/S0040-4020(01)93138-2

The DNP-derivatives of diphenylcyclopropenone 4-azatriafulvenes

E. D. Bergmann^*, I. Agranat

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The reaction of diphenylcyclopropenone and 2,4-dinitrophenylhydrazine in the presence of an acid gives directly either the 2,4-dinitrophenylhydrazone (II) or its salts (VII), The products are interconvertible. The ease of formation of VII from the 4-azatriafulvene derivative II by addition of a proton is explained by the significantly higher contributions, in the ground state, of dipolar structures such as VIIa as compared to IIa. The 4-azatriafulvene cation is characterized by a sharp IR absorption at 1900 cm^-1.

Original language	English
Pages (from-to)	4859-4863
Number of pages	5
Journal	Tetrahedron
Volume	26
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4020(01)93138-2
State	Published - 1970

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abstract = "The reaction of diphenylcyclopropenone and 2,4-dinitrophenylhydrazine in the presence of an acid gives directly either the 2,4-dinitrophenylhydrazone (II) or its salts (VII), The products are interconvertible. The ease of formation of VII from the 4-azatriafulvene derivative II by addition of a proton is explained by the significantly higher contributions, in the ground state, of dipolar structures such as VIIa as compared to IIa. The 4-azatriafulvene cation is characterized by a sharp IR absorption at 1900 cm-1.",

author = "Bergmann, {E. D.} and I. Agranat",

year = "1970",

doi = "10.1016/S0040-4020(01)93138-2",

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N2 - The reaction of diphenylcyclopropenone and 2,4-dinitrophenylhydrazine in the presence of an acid gives directly either the 2,4-dinitrophenylhydrazone (II) or its salts (VII), The products are interconvertible. The ease of formation of VII from the 4-azatriafulvene derivative II by addition of a proton is explained by the significantly higher contributions, in the ground state, of dipolar structures such as VIIa as compared to IIa. The 4-azatriafulvene cation is characterized by a sharp IR absorption at 1900 cm-1.

AB - The reaction of diphenylcyclopropenone and 2,4-dinitrophenylhydrazine in the presence of an acid gives directly either the 2,4-dinitrophenylhydrazone (II) or its salts (VII), The products are interconvertible. The ease of formation of VII from the 4-azatriafulvene derivative II by addition of a proton is explained by the significantly higher contributions, in the ground state, of dipolar structures such as VIIa as compared to IIa. The 4-azatriafulvene cation is characterized by a sharp IR absorption at 1900 cm-1.

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The DNP-derivatives of diphenylcyclopropenone 4-azatriafulvenes

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