The Baeyer-Villiger reaction of some acetylthianaphthene derivatives was written by Matsuki Yasuo;Fujieda, Kunimi. And the article was included in Nippon Kagaku Zasshi in 1967.COA of Formula: C8H4Br2S This article mentions the following:
3-Bromothianaphthene (82.7 g.) in 500 ml. CHCl3 treated with 64 g. Br in 50 ml. CHCl3 for 20 hrs. gave 110.3 g. 2,3-dibromothianaphthene (I). Bromination of thianaphthene yielded 86.2% I. Oxidation of I with H2O2 in AcOHAc2O gave 90% I 1,1-dioxide, m. 156-7°. Similarly 6-acetyl-2,3-dibromothianaphthene 1,1-dioxide (II), m. 187-7.5°, and 6-acetyl-3-bromothianaphthene 1,1-dioxide (III), m. 176-6.5°, were prepared 6-Acetyl-2,3-dibromothianaphthene (IV) (6.6 g.) treated with 0.036 mole F3CCO2H (V) and 0.03 mole H2O2 gave 3.2 g. recovered IV, 0.1 g. 6-acetoxy-2,3-dibromothianaphthene, m. 193-4°, and 2.0 g. II. Similarly 6-acetyl-3-bromothianaphthene (VI) gave 98% III. Treating 1 mole IV with 5 moles F3CCO2OH yielded a 4:1 mixture of II and 6-acetoxy-2,3-dibromothianaphthene 1,1-dioxide, of which hydrolysis gave 2,3-dibromo-6-hydroxythianaphthene 1,1-dioxide, m. 280°. Similarly VI gave a 4:5 mixture of III and 6-acetoxy-3-bromothianaphthene 1,1-dioxide, of which hydrolyis yielded 6-hydroxythianaphthene 1,1-dioxide (VII), m. 228-8.5°. The mechanism of formation of VII is discussed. Oxidation of 2.5 g. VI with 1.3 g. SeO2 in aqueous dioxane yielded 3-bromo-6-thianaphthenylglyoxal, m. 254-5°; quinoxaline derivative m. >300°. Treating VI with 1.28 g. NaN3 5 ml. HOAc, and 0.5 g. concentrated H2SO4 yielded 88.6% 6-acetamido-3-bromothianaphthene, m. 145-6°, and 8% 6-amino-3-bromothianaphthene sulfate, m. 240-5° (decomposition). In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7COA of Formula: C8H4Br2S).
2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.COA of Formula: C8H4Br2S
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem