Further insight into aryl nitration of tetraphenylporphyrin

Zhi Xue; Priscilla P.S. Lee; Yanming Wang; Daniel W J KWONG; Jing Li; John H. Xin; Rick W K WONG; Kevin K.L. Cheuk

doi:10.1016/j.tet.2011.06.031

Further insight into aryl nitration of tetraphenylporphyrin

Zhi Xue, Priscilla P.S. Lee, Yanming Wang, Daniel W J KWONG, Jing Li, John H. Xin, Rick W K WONG^*, Kevin K.L. Cheuk

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

8 Citations (Scopus)

Abstract

We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

Original language	English
Pages (from-to)	6030-6035
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2011.06.031
Publication status	Published - 19 Aug 2011

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

User-Defined Keywords

5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin
Nitration
Porphyrin functionalization
Porphyrin synthesis
Tetra-meso-phenylporphyrin

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10.1016/j.tet.2011.06.031

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title = "Further insight into aryl nitration of tetraphenylporphyrin",

abstract = "We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.",

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T1 - Further insight into aryl nitration of tetraphenylporphyrin

AU - Xue, Zhi

AU - Lee, Priscilla P.S.

AU - Wang, Yanming

AU - KWONG, Daniel W J

AU - Li, Jing

AU - Xin, John H.

AU - WONG, Rick W K

AU - Cheuk, Kevin K.L.

PY - 2011/8/19

Y1 - 2011/8/19

N2 - We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

AB - We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

KW - 5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin

KW - Nitration

KW - Porphyrin functionalization

KW - Porphyrin synthesis

KW - Tetra-meso-phenylporphyrin

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U2 - 10.1016/j.tet.2011.06.031

DO - 10.1016/j.tet.2011.06.031

M3 - Journal article

AN - SCOPUS:79960237665

SN - 0040-4020

VL - 67

SP - 6030

EP - 6035

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Further insight into aryl nitration of tetraphenylporphyrin

Abstract

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