Photodecarboxylation of dicarboxylic acids in the presence of iron(III) chloride

Abstract

The photo-oxidative decarboxylation of succinic, glutaric, and adipic acids with FeCl, yields as principal products, p-chloropropionic acid y-butyrolactone, and 8-chlorovaleric acid, respectively.

Transition metal ion-assisted photochemical generation of alkyl halides and hydrocarbons from carboxylic acids

“…29 Chlorinated products were observed when succinic, glutaric, and adipic acids were photochemically decarboxylated in the presence of FeCl 3 . 28 Here we report the results of our work on some novel aspects of metal-assisted photochemical transformations of carboxylic acids. The majority of work was done with propionic acid owing to its solubility in water, but our mechanistic conclusions should be applicable to longer-chain acids as well.…”

“…These and related issues prompted us to examine iron(III) and copper(II) salts as reagents and potential catalysts for photochemical conversion of carboxylic acids to hydrocarbons and functionalized derivatives. Metal ion-assisted decarboxylation, especially with iron compounds, has already received some attention, [26][27][28][29] but work with copper has been quite limited. 29,30 Several groups demonstrated increased photoreactivity of carboxylic acids in the presence of iron(III).…”

Resolving the Impacts and Feedback of Ocean Optics on Upper Ocean Ecology

“…Algae fall within the spectrally distinct groups depending on which accessory pigments they contain (chlorophyll c-, chlorophyll b-, and phycobilin-containing plasrids). This figure was redrawn and adapted from Delwiche, 1999. photo-oxidation of DOC to DIC in natural waters represents the major identifiable photochemical carbon transformation in the ocean (Kuhnle et al, 1972;Chen et al, 1978;Kotzias et al, 1986;Salonen and Vahatalo, 1994;Graneli et al, 1996;Li et al, 1996;V~hatalo et al, 2000) and suggests a significant oxidation pathway for DOC that bypasses the microbial loop and acts as an independent sink for DOC. The photo-production of DIC appears to be the largest non-biological loss process for DOC in the ocean.…”