Chapter Three - Conclusions
3.1 Conclusions
This research aimed to verify the synthesis protocol for HPA-12 and analogues from aldehydes of Greatrex et al. (2014). Limited success in synthesising required quantities had a negative impact on the outcomes of this research, and no reasons were identified for the low yields that were obtained. Additional time, or resolution of issues resulting in low yields, would have allowed additional research and confirmation of the synthesis protocol. Long reaction times are an issue with this synthesis protocol. However, several steps in the pathway were successful and resulted in the synthesis of reported compounds. Generally, the compounds produced were successfully isolated, and are suitable for use …show more content…
A solution of butadiene and meso-tetraphenylporphyrin (100 mg, 0.162 mmol) dissolved in dichloromethane (100 ml, 1.57 mol) in a water-jacketed flask was irradiated with compact fluorescent lamps. The solution was then concentrated in vacuo and the product subjected to column chromatography to yield the product, aldehyde, and unreacted starting butadiene which could then be recycled.
1-Phenylbutadiene …show more content…
The banana-yellow coloured solution was stirred for 30 minutes, then 1 (6.00 g, 1 equiv, 45.4 mmol) was slowly added over 30 minutes, resulting in a milky brown solution colour. The solution was stirred for a further 18 hours following which two aliquots of hexanes (100ml) were added. The solution was filtered through a pad of silica, and then concentrated in vacuo and the product was purified by column chromatography (10% ethyl acetate in hexanes) to give a colourless oil (1.21 g, 9.30 mmol) Yield 20%, Literature 36 – 89%. 1H NMR (300 MHz, CDCl3) d 7.43-7.41 (m, 2H), 7.35-7.31 (m, 2H), 7.26-7.22 (m, 1H), 6.80 (dd, J = 16, 10 Hz, 1H), 6.58 (d, J = 16 Hz, 1H), 6.52 (dd, J = 17, 10 Hz, 1H), 5.35 (d, J = 17 Hz, 1H), 5.19 (d, J = 10 Hz,
3.1 Conclusions
This research aimed to verify the synthesis protocol for HPA-12 and analogues from aldehydes of Greatrex et al. (2014). Limited success in synthesising required quantities had a negative impact on the outcomes of this research, and no reasons were identified for the low yields that were obtained. Additional time, or resolution of issues resulting in low yields, would have allowed additional research and confirmation of the synthesis protocol. Long reaction times are an issue with this synthesis protocol. However, several steps in the pathway were successful and resulted in the synthesis of reported compounds. Generally, the compounds produced were successfully isolated, and are suitable for use …show more content…
A solution of butadiene and meso-tetraphenylporphyrin (100 mg, 0.162 mmol) dissolved in dichloromethane (100 ml, 1.57 mol) in a water-jacketed flask was irradiated with compact fluorescent lamps. The solution was then concentrated in vacuo and the product subjected to column chromatography to yield the product, aldehyde, and unreacted starting butadiene which could then be recycled.
1-Phenylbutadiene …show more content…
The banana-yellow coloured solution was stirred for 30 minutes, then 1 (6.00 g, 1 equiv, 45.4 mmol) was slowly added over 30 minutes, resulting in a milky brown solution colour. The solution was stirred for a further 18 hours following which two aliquots of hexanes (100ml) were added. The solution was filtered through a pad of silica, and then concentrated in vacuo and the product was purified by column chromatography (10% ethyl acetate in hexanes) to give a colourless oil (1.21 g, 9.30 mmol) Yield 20%, Literature 36 – 89%. 1H NMR (300 MHz, CDCl3) d 7.43-7.41 (m, 2H), 7.35-7.31 (m, 2H), 7.26-7.22 (m, 1H), 6.80 (dd, J = 16, 10 Hz, 1H), 6.58 (d, J = 16 Hz, 1H), 6.52 (dd, J = 17, 10 Hz, 1H), 5.35 (d, J = 17 Hz, 1H), 5.19 (d, J = 10 Hz,