Development of an Intramolecular Aryne Ene Reaction and Application to the Formal Synthesis of (±)-Crinine was written by Candito, David A.;Dobrovolsky, Dennis;Lautens, Mark. And the article was included in Journal of the American Chemical Society in 2012.Formula: C8H6BrFO2 This article mentions the following:
A general and high yielding annulation strategy for the synthesis of various carbo- and heterocycles, based on an intramol. aryne ene reaction is described. It was found that the geometry of the olefin is crucial to the success of the reaction, with exclusive migration of the trans-allylic-H taking place. Furthermore, the electronic nature of the aryne was found to be important to the success of the reaction. Deuterium labeling studies and DFT calculations provided insight into the reaction mechanism. The data suggests a concerted asynchronous transition state, resembling a nucleophilic attack on the aryne. This strategy was successfully applied to the formal synthesis of the ethanophenanthridine alkaloid (±)-crinine. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Formula: C8H6BrFO2).
Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Formula: C8H6BrFO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary