Antimalarials. 2,5-Diphenyl-3-furyl Amino Ketones and Alcohols<sup>1</sup>

Lutz, Robert E.; Rowlett, Russell J.

doi:10.1021/ja01184a022

Cited by 18 publications

(3 citation statements)

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“…, ,) + F FOi (8) This scheme allows for three possible mechanisms for photooxidation: via singlet substrate (ksox), triplet substrate (kt0x), and singlet oxygen (k00x). In other respects, it is substantially simpler than the full range of photoprocesses that could follow the initial excitation step, based on the following observations.…”

Section: Kinetic Analysismentioning

confidence: 99%

Photooxidation of isobenzofurans. Dual mechanism process

Olmsted¹,

Akashah²

1973

J. Am. Chem. Soc.

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The photooxidation of several substituted isobenzofurans has been studied. Kinetic behavior at low substrate concentrations shows that a second mechanism other than that involving singlet oxygen is operative, and the absence of azulene quenching demonstrates that the second mechanism involves direct addition of oxygen to excited singlet isobenzofuran. Rate constants for this singlet substrate-ground state oxygen reaction are in the range of 10 M_1 sec-1 and the mechanism is calculated to contribute about 10% of the photooxidation at high isobenzofuran concentration, ranging upward to virtually 100% at lower substrate concentrations. The mechanism is suggested to be via charge-transfer rather than concerted addition and the possibility of such an oxidation mechanism is generalized to other aromatic systems.A great deal of evidence has been amassed in the past few years to indicate that photoinduced addition of molecular oxygen to several types of substrates proceeds primarily if not exclusively via excited oxygen molecules in the (^g) electronic state.2

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Section: Kinetic Analysismentioning

confidence: 99%

Photooxidation of isobenzofurans. Dual mechanism process

Olmsted¹,

Akashah²

1973

J. Am. Chem. Soc.

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“…Chem. Soc., 75, 393(1953) tc E. In the reduction of 1, 2-dibenzoylethylene [l a, b] with aluminum isopropoxide, the addition of aluminum chloride increased the yields of furan derivatives [5], [6 ] or [7]. The cis-isomer was isomerized to trans-under the reduction conditions.…”

mentioning

confidence: 99%

“…The structures of products [6], [7], [9] and [10] were established on the basis of spectral data (Table 5).…”

mentioning

confidence: 99%

Reduction of cis- and trans-1,2-dibenzoylethylene and cis-.ALPHA.,.BETA.-dibenzoylstyrene with a combination of aluminum isopropoxide and aluminum chloride.

ヤサ¹,

裕²

1985

NIPPON KAGAKU KAISHI

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Neuere präparative Methoden der organischen Chemie III. Synthesen unter Verwendung von Diazoketonen

Weygand¹,

Bestmann²

1960

Angewandte Chemie

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Diese Zusarnrnenfassung, bei der auch eigene, bisher unpublizierte Arbeiten berucksichtigt werden, fuhrt von den Aliphaten uber die Kohlenhydrate und Peptide zu isocyclischen und heterocyclischen Verbindungen. Die Vielfalt der behandelten Stoffe zeigt die groOe Anwendungsbreite der Diazoketone als Hilfsmittel fur Synthesen. Die auBerordentliche Reaktionsfreudigkeit der a-Diazo-carbonyl-Verbindungen l a O t noch viele Bereicherungen der praparativen, wie auch der theoretischen organischen Chernie erwarten. A. Einleitung B. Reaktionsweisen der Diazoketorte 1. Stickstoff-Abspaltung aus Diazoket.onen *) W . Bradley u. R. Robinson, J. chem. SOC. [London] 7928, 1310. a) B. Eistert in: Neuere Methoden der pri4parativen organischen

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Antimalarials. 2,5-Diphenyl-3-furyl Amino Ketones and Alcohols¹

Cited by 18 publications

References 0 publications

Photooxidation of isobenzofurans. Dual mechanism process

Photooxidation of isobenzofurans. Dual mechanism process

Reduction of cis- and trans-1,2-dibenzoylethylene and cis-.ALPHA.,.BETA.-dibenzoylstyrene with a combination of aluminum isopropoxide and aluminum chloride.

Neuere präparative Methoden der organischen Chemie III. Synthesen unter Verwendung von Diazoketonen

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Antimalarials. 2,5-Diphenyl-3-furyl Amino Ketones and Alcohols1

Cited by 18 publications

References 0 publications

Photooxidation of isobenzofurans. Dual mechanism process

Photooxidation of isobenzofurans. Dual mechanism process

Reduction of cis- and trans-1,2-dibenzoylethylene and cis-.ALPHA.,.BETA.-dibenzoylstyrene with a combination of aluminum isopropoxide and aluminum chloride.

Neuere präparative Methoden der organischen Chemie III. Synthesen unter Verwendung von Diazoketonen

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Antimalarials. 2,5-Diphenyl-3-furyl Amino Ketones and Alcohols¹