Reaction Mechanism
The reaction mechanism of the Gassman indole synthesis is divided among three steps.
The first step is the oxidation of the aniline 1 using tert-butyl hypochlorite (tBuOCl) to give the chloramine 2.
The second step is the addition of the ketone to give the sulfonium ion 3, and is typically done at low temperatures (-78 °C).
The third and final step is the addition of a base, which in this case is triethylamine. Upon warming to room temperature, the base will deprotonate the sulfonium ion creating the sulfonium ylide 4, which quickly undergoes a -sigmatropic rearrangement to give the ketone 5. The ketone 5 will undergo a facile condensation to give the desired 3-thiomethylindole 6.
Read more about this topic: Gassman Indole Synthesis
Famous quotes containing the words reaction and/or mechanism:
“In contrast to revenge, which is the natural, automatic reaction to transgression and which, because of the irreversibility of the action process can be expected and even calculated, the act of forgiving can never be predicted; it is the only reaction that acts in an unexpected way and thus retains, though being a reaction, something of the original character of action.”
—Hannah Arendt (1906–1975)
“I’ve never known a Philadelphian who wasn’t a downright “character;” possibly a defense mechanism resulting from the dullness of their native habitat.”
—Anita Loos (1888–1981)