LE3 .A278 2014

2014

Lukeman, Matthew

Acadia University

Bachelor of Science

Honours

Chemistry

Chemistry

m-Nitrophenylpropionic acids, while still in the initial stages of work, have been shown to be good photoremovable protecting groups. One in particular is 3-hydroxy-2-methyl-2-(3-nitrophenyl)propanoic acid, 51, which has been previously shown to release halide ions rapidly, with good aqueous solubility and have only one photoproduct formed after irradiation. We also attempted to use this chromophore to release carboxylic acids in a similar fashion. 51 was successfully synthesised via a 7 step synthesis by starting with 44 and converting it to 45 with a 97% yield. 45 was then converted to 51 by sequentially synthesising products 46, 47, 48, 49, 50 and 51 with yields of 95%, 86%, %, 81%, 87%, and 86% were obtained respectively. 51 was then used to protect acetic acid to give product 52. A yield of 92% was realized for this step and an overall yield of 30% was obtained. The photochemistry of 53 was then studied with UV-Vis, 1H and 13C{1H} NMR spectroscopy. It was found that when 53 is irradiated with 300 nm light under near biological conditions, only one photoproduct, 55 is formed. This makes 53 a potential candidate for carboxylic acid photorelease with possible biological applications. 1

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https://scholar.acadiau.ca/islandora/object/theses:1169