Monophosphaporphyrins: Oxidative π-extension at the peripherally fused carbocycle of the phosphaporphyrin ring

Yoshihiro Matano; Makoto Nakashima; Takashi Nakabuchi; Hiroshi Imahori; Shinya Fujishige; Haruyuki Nakano

doi:10.1021/ol7029118

Monophosphaporphyrins: Oxidative π-extension at the peripherally fused carbocycle of the phosphaporphyrin ring

Yoshihiro Matano, Makoto Nakashima, Takashi Nakabuchi, Hiroshi Imahori, Shinya Fujishige, Haruyuki Nakano

Multidisciplinary chemistry

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

44 Citations (Scopus)

Abstract

The 18π-σ^3- and 22π-σ⁴- phosphaporphyrins were successfully prepared by an acid-promoted condensation between a phosphatripyrrane and a 2,5-bis[hydroxy(phenyl)methyl]pyrrole, and their structures, aromaticity, and optical and electrochemical properties were disclosed. Notably, a σ⁴-phosphaporphyrinogen and the 18π-σ³-phosphaporphyrin undergo oxidative π-extension at the peripherally fused carbocycle to afford the 22π-σ⁴- phosphaporphyrin.

Original language	English
Pages (from-to)	553-556
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	4
DOIs	https://doi.org/10.1021/ol7029118
Publication status	Published - Feb 21 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol7029118

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title = "Monophosphaporphyrins: Oxidative π-extension at the peripherally fused carbocycle of the phosphaporphyrin ring",

abstract = "The 18π-σ3- and 22π-σ4- phosphaporphyrins were successfully prepared by an acid-promoted condensation between a phosphatripyrrane and a 2,5-bis[hydroxy(phenyl)methyl]pyrrole, and their structures, aromaticity, and optical and electrochemical properties were disclosed. Notably, a σ4-phosphaporphyrinogen and the 18π-σ3-phosphaporphyrin undergo oxidative π-extension at the peripherally fused carbocycle to afford the 22π-σ4- phosphaporphyrin.",

author = "Yoshihiro Matano and Makoto Nakashima and Takashi Nakabuchi and Hiroshi Imahori and Shinya Fujishige and Haruyuki Nakano",

year = "2008",

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doi = "10.1021/ol7029118",

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journal = "Organic Letters",

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T1 - Monophosphaporphyrins

T2 - Oxidative π-extension at the peripherally fused carbocycle of the phosphaporphyrin ring

AU - Matano, Yoshihiro

AU - Nakashima, Makoto

AU - Nakabuchi, Takashi

AU - Imahori, Hiroshi

AU - Fujishige, Shinya

AU - Nakano, Haruyuki

PY - 2008/2/21

Y1 - 2008/2/21

N2 - The 18π-σ3- and 22π-σ4- phosphaporphyrins were successfully prepared by an acid-promoted condensation between a phosphatripyrrane and a 2,5-bis[hydroxy(phenyl)methyl]pyrrole, and their structures, aromaticity, and optical and electrochemical properties were disclosed. Notably, a σ4-phosphaporphyrinogen and the 18π-σ3-phosphaporphyrin undergo oxidative π-extension at the peripherally fused carbocycle to afford the 22π-σ4- phosphaporphyrin.

AB - The 18π-σ3- and 22π-σ4- phosphaporphyrins were successfully prepared by an acid-promoted condensation between a phosphatripyrrane and a 2,5-bis[hydroxy(phenyl)methyl]pyrrole, and their structures, aromaticity, and optical and electrochemical properties were disclosed. Notably, a σ4-phosphaporphyrinogen and the 18π-σ3-phosphaporphyrin undergo oxidative π-extension at the peripherally fused carbocycle to afford the 22π-σ4- phosphaporphyrin.

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JO - Organic Letters

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Monophosphaporphyrins: Oxidative π-extension at the peripherally fused carbocycle of the phosphaporphyrin ring

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