Photodecarboxylation of benzyl esters

Givens, Richard S.; Oettle, W. Frederick

doi:10.1021/ja00742a043

Cited by 29 publications

(19 citation statements)

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“…We believe these data constitute a rigorous chemicalspectroscopic proof of the structures of 10,11-anhydroerythromycin B (2), 8-epz-10,l 1-anhydroerythromycin B (4), and 8-e^z-erythromycin B (6). Circular dichroism correlations have confirmed the previous configurational assignments5 to the Cs epimeric 3,5-di-O-acetyl-10,ll-anhydroerythronolides B.…”

Section: Testssupporting

confidence: 80%

C-8 Epimeric 10,11-anhydroerythromycins A and the C-8 epimeric 11,12-epoxyerythromycins A

Tadanier¹,

Martin²,

Egan³

et al. 1973

J. Am. Chem. Soc.

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Section: Testssupporting

confidence: 80%

C-8 Epimeric 10,11-anhydroerythromycins A and the C-8 epimeric 11,12-epoxyerythromycins A

Tadanier¹,

Martin²,

Egan³

et al. 1973

J. Am. Chem. Soc.

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“…This system also undergoes irreversible photochemistry. By irradiating at 254 nm, a decarboxylation reaction [168][169][170] takes place and the lactone can no longer be formed. This essentially offers the potential to design a thermochromic system, the function of which can be interrupted by means of light input, see Scheme 33.…”

Section: Thermochromism In Flavylium Derivativesmentioning

confidence: 99%

Chemistry and applications of flavylium compounds: a handful of colours

et al. 2012

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Flavylium compounds are versatile molecules that comprise anthocyanins, the ubiquitous colorants used by Nature to confer colour to most flowers and fruits. They have found a wide range of applications in human technology, from the millenary colour paints described by the Roman architect Vitruvius, to their use as food additives, combining colour and antioxidant effects, and even as light absorbers in solar cells aiming at a greener solar energy conversion. Their rich complexity derives in part from their ability to switch between a variety of species (flavylium cations, neutral quinoidal bases, hemiketals and chalcones, and negatively charged phenolates) by means of external stimuli, such as pH, temperature and light. This critical review describes (i) the historical advancements in the understanding of the equilibria of their chemical reaction networks; (ii) their thermodynamics and kinetics; (iii) the mechanisms underlying their colour development, such as co-pigmentation and host-guest interactions; (iv) the photophysics and photochemistry that lead to photochromism; and (v) applications in solar cells, models for optical memories, photochromic soft materials such as ionic liquids and gels, and their properties in solid state materials (274 references).

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“…The synthetic utility and generality of the ODPM reaction of bicyclo[2.2.2]octenone is illustrated by the examples collected inTable 16, including yields and references 67,68,[107][108][112][113][115][116][117][118][119][120][121][122] However, it should be pointed out that there are limitations in the type of substitution that can be present in the bicyclo[2.2.2]-octenone skeleton.…”

mentioning

confidence: 99%