Homolytic Base-Promoted Aromatic Alkylations by Alkylmercury Halides was written by Russell, Glen A.;Chen, Ping;Kim, Byeong Hyo;Rajaratnam, Ragine. And the article was included in Journal of the American Chemical Society in 1997.Safety of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:
Electron transfer chain reactions leading to substitution in electronegatively substituted benzene derivatives can be observed with alkylmercury halides in the presence of proton acceptors such as DABCO. Promotion by base involves the abstraction of a proton from the substituted cyclohexadienyl adduct radical to form a radical anion which readily transfers an electron to RHgX with the regeneration of Râ? Aromatic substitutions involving Me3Câ?are highly regioselective and yield products of only para attack for PhCHO, PhCOMe, PhCOCMe3, PhCOPh, PhCN, phthalimides, or 1,2-dicyanobenzene. The ortho/para substitution products are observed for isophthalaldehyde or 1,3-dicyanobenzene, while 1,4-dicyanobenzene yields the ortho substitution product. At 25-35° substitution by Me3Câ?ortho to an ester group is not observed and m- or p-cyanobenzoate esters yield only products of substitution ortho to the cyano group. With Me2CHâ?substitution ortho to the ester function is observed with di-Et isophthalate. Intramol. radical cyclizations of the radical adducts of 1-aryl-4-penten-1-ones leading to α-tetralones is also promoted by the presence of DABCO. When the aryl group contains a para ester function, spirocyclization occurs leading to a rearrangement acyl radical which can be oxidized by Me3CHgCl to the acyl cation and the carboxylic acid. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Safety of 2-(Phenylthio)isoindoline-1,3-dione).
2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Safety of 2-(Phenylthio)isoindoline-1,3-dione
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles