Synthesis of Stable 1‐Benzothiepins

Seven-membered heterocycles. 9. Synthesis and properties of some 5-alkyl and 5-aryl derivatives of 1-benzothiepin

“…Caled for CieHisClOS: C, 66.54; H, 4.53; Cl, 12.28. Found: C, 66.44; H, 4.44; Cl, 12.00. 7a-Bromo-7-hydroxy-7-phenylcyclopropa[b][l]benzothiopyran (5). Using the same procedure described for the preparation of 4, 7a-bromocyclopropa[b][l]benzothiopyran-7-one14 (0.85 g, 3.9 mmol) provided, after recrystallization from cyclohexane, 280 mg (22%) of 5: mp 129-131 °C; IR (CHC13) 3565 cm"1 (OH); NMR (CDCI3) 1.6 (dd, 2, J = 8 Hz, Ci H's), 3.1 (m, 2, OH, Cia H's), 7.2-7.9 (m, 9, aromatic H's).…”

“…Found: C, 50.22; , 3.20; S, 8.19. 2-Bromo-4-chloro-5-benzyl-2,3-dihydro-l-benzothiepin 1,1-Dioxide (33). Following the procedure described for the preparation of 23, 5-benzyl-2-bromo-4-chloro-2,3-dihydro-l-benzothiepin (1.00 g, 2.7 mmol) gave, after recrystallization from 95% ethanol and benzene, 0.68 g (67%) of 33: mp 181-183 °C; IR (CHC13) 1325 and 1115 cm"l (S02); NMR (CDC13) 3.21 (m, 2, C3 H's), 4.11 (s, 2, C6H5CH2), 5.49 (dd, 2, JC2-C31 = 6 Hz, Jc2-c3, = 10 Hz, C2 H's), 7.2-7.8 (m, 8, aromatic H's except C9 H), 8.20 (m, 1, C9 H). Recrystallization from 95% ethanol and benzene gave an analytical sample, mp 182-183 °C.…”

Organometallic Chemistry

“…After the Abitur, his final secondary school examinations in 1966, he studied chemistry at the University of Erlangen-Nuremberg. In 1973, he received a doctorate with honors for his research on photochemical reactions of oxepin and thiepin derivatives in the group of Hans Hofmann [4][5][6][7][8]10,12,18]. Despite their identical family names, he and his doctoral supervisor were not related; Hof(f)mann is an unusually prevalent surname among distinguished German chemists.…”

Determination of fentanyl and related compounds by capillary gas chromatography with electron capture detection

“…In that work it was shown that the reaction does not proceed in the absence of base or even in the presence of pyridine. High-yield derivatization requires the presence of a base such as 4-DMAP, suggesting the effective oxidizing and acylating species to be the N-(heptafluorobutyry 1)-4-(dimethylamino)pyridinium ion (23).…”