Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins

Ravindra K. Pandey; Fuu Yau Shiau; Meden Isaac; S. Ramaprasad; Thomas J. Dougherty; Kevin M. Smith

doi:10.1016/S0040-4039(00)74751-4

Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins

Ravindra K. Pandey
, Fuu Yau Shiau
, Meden Isaac
, S. Ramaprasad
, Thomas J. Dougherty
, Kevin M. Smith

Institute for Lasers Photonics and Biophotonics

University of California at Davis
University of Arkansas for Medical Sciences
Roswell Park Cancer Institute

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

31 Scopus citations

Abstract

Regiospecificity of pyrrole subunit OsO₄ oxidation in porphyrins is affected significantly by the presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities.

Original language	English
Pages (from-to)	7815-7818
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(00)74751-4
State	Published - Dec 5 1992

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@article{43320ded099c476abc79b73c7aa2cba1,

title = "Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins",

abstract = "Regiospecificity of pyrrole subunit OsO4 oxidation in porphyrins is affected significantly by the presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities.",

author = "Pandey, \{Ravindra K.\} and Shiau, \{Fuu Yau\} and Meden Isaac and S. Ramaprasad and Dougherty, \{Thomas J.\} and Smith, \{Kevin M.\}",

year = "1992",

month = dec,

day = "5",

doi = "10.1016/S0040-4039(00)74751-4",

language = "English",

volume = "33",

pages = "7815--7818",

journal = "Tetrahedron Letters",

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number = "51",

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TY - JOUR

T1 - Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements

T2 - Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins

AU - Pandey, Ravindra K.

AU - Shiau, Fuu Yau

AU - Isaac, Meden

AU - Ramaprasad, S.

AU - Dougherty, Thomas J.

AU - Smith, Kevin M.

PY - 1992/12/5

Y1 - 1992/12/5

N2 - Regiospecificity of pyrrole subunit OsO4 oxidation in porphyrins is affected significantly by the presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities.

AB - Regiospecificity of pyrrole subunit OsO4 oxidation in porphyrins is affected significantly by the presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities.

UR - https://www.scopus.com/pages/publications/0027080926

U2 - 10.1016/S0040-4039(00)74751-4

DO - 10.1016/S0040-4039(00)74751-4

M3 - Article

AN - SCOPUS:0027080926

SN - 0040-4039

VL - 33

SP - 7815

EP - 7818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins

Abstract

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