The meso-reactivity of porphyrins and related compounds. Part IV. Introduction of oxygen functions

Bonnett, Raymond; Dimsdale, M. J.; Stephenson, G. F.

doi:10.1039/j39690000564

Cited by 50 publications

(21 citation statements)

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“…89,90 The use of OsO 4 in the presence of pyridine to form the vicinal diol followed by acid-mediated pinacol rearrangement was implemented by Inhoffen 87,91 and by Chang. 92,93 …”

Section: Early Landmarks In Chlorin Chemistrymentioning

confidence: 99%

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

2015

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Woodward reported his infamous synthesis of chlorin e 6 trimethyl ester, a known synthetic precursor to chlorophyll a. [59][60][61][62][63][64]124 The work was posited on a half-century of intensive studies by many investigators in tetrapyrrole chemistry and began a decade after the close of Fischer's lifetime of research 125−128 (which included an uncompleted synthetic program directed toward chlorophylls 15 ). Indeed, "he read all the umpteen papers on the chlorophylls written by Willstaẗter and Fischer, including the experimental parts." 129 The Woodward synthesis of chlorin e 6 trimethyl ester required 46 steps, of which 24 were spent on converting the sole precursor, Knorr's pyrrole, to the four pyrroles destined to form rings A−D; 7 additional steps accrued to obtain the dipyrromethanes that constitute the Eastern and Western halves (Scheme 13, the step numbers are identical to those shown in ref 64.). The first step formed the Knorr pyrrole (in several kg quantities), the next 24 steps were divided into four parallel paths, whereas the remaining 21 steps proceeded in linear fashion. Remarkable features of the synthesis include the directed intramolecular joining (via an imine) of the Eastern and Western halves (step 33), construction of the acrylate Scheme 10. Hydrogenation of a Porphyrin to Form a Chlorin Scheme 11. Representative meso-Tetraarylchlorins Scheme 12. Methyl Pyropheophorbide a

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“…89,90 The use of OsO 4 in the presence of pyridine to form the vicinal diol followed by acid-mediated pinacol rearrangement was implemented by Inhoffen 87,91 and by Chang. 92,93 …”

Section: Early Landmarks In Chlorin Chemistrymentioning

confidence: 99%

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

2015

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“…The substance was identical with that obtained earlier. 3 The proton-decoupled 13C n.m.r. spectrum of the methanol adduct showed eighteen signals as expected.…”

Section: Et Omementioning

confidence: 99%

On the structure of the alkanol propentdyopent adducts

Bonnett¹,

Ioannou²

1986

J. Chem. Soc., Chem. Commun.

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“…shape) of electronic spectra, were compared with a variety of synthesized and reported chlorins. Chlorin-636 exhibits spectral and chromatographic characteristics akin to the following tetrapyrrole pigments: dihydro-DPEP (λi = 640 nm) (Blummer and Omenn, 1961); 7-oxo-octaethylchlorin (λi = 642 nm) (Bonnett et al, 1969); dioxymesoporphyrin-IX (λi = 644 nm) and dioxydeoxophylloerythrin (k { = 640 nm) (Baker and Smith, 1974); and deoxomesopyropheophorbide-α CK\ = 638 nm). The majority of the preceding pigments exhibit electronic spectra in which either the position of the Soret band is shifted to higher energy or Band III is missing, or both.…”

Section: Chlorin-636mentioning

confidence: 99%

The meso-reactivity of porphyrins and related compounds. Part IV. Introduction of oxygen functions

Cited by 50 publications

References 0 publications

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

On the structure of the alkanol propentdyopent adducts

Products of Chlorophyll Diagenesis in Japan Trench Sediments, Deep Sea Drilling Project Sites 438, 439, and 440

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