The Photoöxidation of Tetracyclone

Bikales, Norbert M.; Becker, Ernest I.

doi:10.1021/jo01118a020

Cited by 29 publications

(14 citation statements)

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“…Repeated recrystallization yielded a product which gave a melting point much closer to the literature value ( Table 2). UV and IR spectra were consistent with literature data (Bikales and Becker, 1956). On reapplication of either isomer to TLC plates, trace amounts of the other isomer were observed.…”

supporting

confidence: 89%

“…3a, Kondo et al, 1971) and the photooxidation of tetracyclone (Fig. 3b, Bikales and Becker, 1956). Brown and King (1975) have recently developed a technique using '"0 labelled molecular oxygen to further probe the mechanism of such reactions.…”

Section: Introductionmentioning

confidence: 89%

“…However the photooxidation of tetracyclone (2,3,4,5,-tetraphenyIcyclopentadienone, Fig. 2a) is formally analogous to the conversion of oxyheme to biliverdin, since both reactions involve decarbonylation and incorporation of two new carbonyl oxygen atoms into the product (Coan et a/., 1953; Duffraise et a/., 1954; Bikales and Becker, 1956). The photooxidation of tetracyclone can occur both with and without the addition of external '02 sensitizers.…”

Section: Introductionmentioning

confidence: 99%

“…Wilcox and Stevens (1962) have shown that photooxidation in the presence of UV filtered light gives a high yield of cis dibenzoyl stilbene, whereas photooxidation with UV unfiltered light yields varying amounts of cis and trans isomers depending upon reaction conditions. The formation of the more thermodynamically favourable trans isomer is almost certainly due to a secondary photoisomerization of the cis isomer, stimulated by its absorption in the near UV region (Kuhn et a/., 1950; Bikales and Becker, 1956).…”

Section: Introductionmentioning

confidence: 99%

“…irrigated with xylene and dried in an oven at 70°C for 2.5 h, to give a complex mixture from which trans dibenzoyl stilbene (72.8mg) and cis dibenzoyl stilbene (121 mg) were isolated. The trans isomer was purified by recrystallbation from chloroform/petroleum ether as white crystals (42.9 mg), melting at 228-229°C (literature value is 229.7-231.6"C. Bikales and Becker, 1956). UV and IR spectra were also in agreement.…”

mentioning

confidence: 99%

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A STUDY OF THE UNSENSITIZED PHOTOOXIDATION OF TETRACYCLONE BY ¹⁸O LABELLING

Chaney

Brown

1978

Photochem & Photobiology

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Abstract. The photooxidation of tetracyclone yielding dibenzoyl stilbene was studied by means of an 18O labelling method recently used to study heme catabolism. Unlike heme degrading systems, the photooxidation of tetracyclone was found to proceed by a one‐molecule mechanism whereby both oxygen atoms in dibenzoyl stilbene are derived from the same molecule of molecular oxygen. This is evidence for a dioxobridged intermediate.

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supporting

confidence: 89%

Section: Introductionmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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A STUDY OF THE UNSENSITIZED PHOTOOXIDATION OF TETRACYCLONE BY ¹⁸O LABELLING

Chaney

Brown

1978

Photochem & Photobiology

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Sensitized Photooxygenation of Olefins

Denny

Nickon

2011

Organic Reactions

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Sensitized photooxygenations of olefins have been extensively studied; they represent convenient methods for the introduction of oxygen at specific sites. When an aerated solution containing a monolefin, diene, or polyene, and a sensitizer is irradiated with light that can be absorbed by the sensitizer, oxygenated products are formed whose nature depends upon the structure of the substrate and the lability of the initial photoproducts under the reaction conditions. The ready reducibility of hydroperoxides to alcohols enhances the synthetic usefulness of these photoxygenations In this chapter, coverage is restricted to molecules with one or more carbon‐carbon double bonds.

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