Red Luma

 

Find 3 papers that are related to the mechanism for this reaction, then pick one paper and Briefly (150-250 words, plus pictures) indicate what its conclusions are about the mechanism.


In the article by Dimitris Noutsias, Antonia Kouridaki, and Gergios Vassilikogiannakis, a structure undergoes ketalization with acid to rapidly form the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. From this framework, one can easily synthesize 2-hydroxy-exo-brevicomin, which happens to be a pheromone of the Western Pine Beetle. The reaction (shown below) takes place in a DMS (Dimethyl Sulfate) solution at a temperature of 5 degrees Celsius. The acid used in this reaction is p-TsOH (p-Toluenesulfonic Acid). This protonates the hydroxyl group that is not attached to the Furan Diol, which facilitates the ketal reaction. It is a photochemical reaction, more specifically, a photooxygenation reaction, which is a light-induced oxidation reaction in which molecular oxygen is incorporated into the product.
The reason that this is important is that it is a much faster and more selective methodology then the older synthesis of the product.

 

Noutsias, D.; Kouridaki, A.; Vaasilikogiannakis, G. Org. Lett. 2011, 13, 1166-1169.

 

List up to three papers that have cited the paper you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author decided to cite the work.


Yan, Z.; Wei, W.; Xun, H.; Anguo, S. Chem. Lett. 2012, 41, 1500-1502.
This author chose to cite the article because it also deals with photooxygenation reactions.


Noutsias, D.; Alexopoulou, I.; Montagnon, T.; Vaasilikogiannakis, G. Green Chem. 2012,14, 601-604.
This author cited the article because there are multiple authors that worked on both papers, and it also involves photooxygenation reactions.


Yin, B.; Zeng, G.; Cai, C.; Ji, F.; Huang, L.; Li, Z.; Jiang, H. Org. Lett. 2012, 14, 616-619.
These authors decided to cite this article because the article also has a reaction that involves forming furans within an individual molecule.