REFERENCES


Reference1

The reaction carried out by M.E.W. investigated the formation of vinyl triflates form carbonyl compounds and triflic anhydride. The experiments tested aldehydes and ketones, running the reaction in different solvents and at different temperatures. In discovering the quantity of the desired species, 13C, 19F, and 1H NMR spectroscopy were utilized to further understand the mechanism of the formation of vinyl triflates.

Reference2

In order to successfully convert aldol-susceptible carbonyl compounds, a polar solvent and higher reaction temperatures were required. The conversion of the carbonyl has shown to be very temperature and solvent dependent. Carbonyl compounds which were not aldol-susceptible did not require high temperatures and a polar solvent for a successful conversion into vinyl triflates. The higher temperatures and polar solvent does reduce reaction times and there is no change in overall yield. Tf2O attaches to the ketone or carbonyl, second OTf attaches electrophilic carbon, elimination and the double bond is formed with the resulting vinyl triflate.


R E F E R E N C E

Wright, M. E.; Pulley, S. R. J. Org. Chem. 1989, 54, 2886-2889.



C I T I N G   P A P E R S

1. Kutsumura, N.; Shibuya, K.; Yamaguchi, H.; Saito, T. Tetrahedron Lett. 2017, 58, 4099-4102.

This paper explains the key to the mechanism, electron-withdrawing inductive effects, behind the regioselective reaction of vicinal bis-triflate elimination, and cited the original paper to explain the formation of vinyl triflate formation which is used.


2. Wang, X.; Studer, A. J. Am. Chem. Soc. 138, 9, 2977-2980.

This paper uses Fe catalysts in the vicinal cyanotriflation to allow for desired regio and stereoselectivity, making this method highly valuable, and cited the original paper to explain regioselectivity of this reaction.


3. Chassaing, S.; Specklin, S.; Weibel, J.M.; Pale, P. Current Organic Synthesis 2012, 9, 806-827.

This paper analyzes and explains the current methods of synthesizing vinyl and aryl sulfonates, and cited this paper to explain more classical methods of synthesizing these compounds, with an emphasis on reaction mechanisms.