Photochemical Intramolecular C-H Addition of Dimesityl(hetero)arylboranes by a [1,6]-Sigmatropic Rearrangement was written by Ando, Naoki;Fukazawa, Aiko;Kushida, Tomokatsu;Shiota, Yoshihito;Itoyama, Shuhei;Yoshizawa, Kazunari;Matsui, Yasunori;Kuramoto, Yutaro;Ikeda, Hiroshi;Yamaguchi, Shigehiro. And the article was included in Angewandte Chemie, International Edition in 2017.Synthetic Route of C6H8S The following contents are mentioned in the article:
A new reaction mode for triarylboranes under photochem. conditions was discovered. Photoirradiation of dimesitylboryl-substituted (hetero)arenes produced spirocyclic boraindanes, where one of the C-H bonds in the ortho-Me groups of the mesityl substituents was formally added in a syn fashion to a C-C double bond of the (hetero)aryl group. Quantum chem. calculations and laser flash photolysis measurements indicated that the reaction proceeds by a [1,6]-sigmatropic rearrangement. This behavior is reminiscent of the photochem. reaction mode of arylalkenylketones, thus demonstrating the isosteric relation between tricoordinate organoboron compounds and the corresponding pseudo-carbocationic species in terms of pericyclic reactions. Despite the disrupted π-conjugation, the resulting spirocyclic boraindanes exhibited a characteristic absorption band at relatively long wavelengths (λ=370-400 nm). This study involved multiple reactions and reactants, such as 2,5-Dimethylthiophene (cas: 638-02-8Synthetic Route of C6H8S).
2,5-Dimethylthiophene (cas: 638-02-8) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is also used in the manufacturing of dyes such as thioindigo.Synthetic Route of C6H8S
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem