SUBSTITUENT EFFECTS IN TETRAPYRROLE SUBUNIT REACTIVITY AND PINACOL-PINACOLONE REARRANGEMENTS - VIC-DIHYDROXYCHLORINS AND VIC-DIHYDROXYBACTERIOCHLORINS

被引：30

作者：

PANDEY, RK

SHIAU, FY

ISAAC, M

RAMAPRASAD, S

DOUGHERTY, TJ

SMITH, KM

机构：

[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616

[2] ROSWELL PK CANC INST,DEPT RADIAT MED,BUFFALO,NY 14263

[3] UNIV ARKANSAS MED SCI HOSP,DEPT RADIOL & PATHOL,LITTLE ROCK,AR 72205

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)74751-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：7815 / 7818

页数：4

共 18 条

[1] 2ND GENERATION TUMOR PHOTOSENSITIZERS - THE SYNTHESIS AND BIOLOGICAL-ACTIVITY OF OCTAALKYL CHLORINS AND BACTERIOCHLORINS WITH GRADED AMPHIPHILIC CHARACTER
ADAMS, KR
BERENBAUM, MC
BONNETT, R
NIZHNIK, AN
SALGADO, A
VALLES, MA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (12): : 1465 - 1470
[2] SECOND GENERATION TUMOR PHOTOSENSITIZERS - THE SYNTHESIS OF OCTA-ALKYL CHLORINS AND BACTERIOCHLORINS WITH GRADED AMPHIPHILIC CHARACTER
BONNETT, R
NIZHNIK, AN
BERENBAUM, MC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1822 - 1823
[3] BONNETT R, 1964, P CHEM SOC LONDON, P371
[4] BONNETT R, 1969, J CHEM SOC C, P567
[5] DIFFERENTIATION OF BACTERIOCHLORIN AND ISOBACTERIOCHLORIN FORMATION BY METALATION - HIGH-YIELD SYNTHESIS OF PORPHYRINDIONES VIA OSO4 OXIDATION
CHANG, CK
SOTIRIOU, C
WU, W
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (15) : 1213 - 1215
[6] MIGRATORY APTITUDES IN PINACOL REARRANGEMENT OF VIC-DIHYDROXYCHLORINS
CHANG, CK
SOTIRIOU, C
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (06) : 1739 - 1741
[7] DOUGHERTY TJ, 1976, CANCER RES, V38, P3628
[8] FISHER H, 1944, LIEBIGS ANN CHEM, V556, P131
[9] FISHER H, 1937, CHEM PYRROLS 1, V2, P269
[10] INHOFFEN HH, 1969, LIEBIGS ANN CHEM, V725, P167

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