cis‐Triaza‐tris‐σ‐homobenzol (cis‐„Benzol‐triimin”︁)

Abstract

Bleitetraacetat (CH,C12; O T ) zum Thiadiazolin (7) dehydriert. Nach der anschlieBenden Behandlung mit Triithylphosphit (80°C) isoliert man durch praparative Schichtchromatographie (Kieselgel, Pentan) ca. 20% (3) [bezogen auf ( 4 ) ] als farblose, leicht sublimierbare Prismen. Unter der Einwirkung katalytischer Mengen des Palla-

Addition of singlet oxygen to arene oxides

“…Trituration with ether gave white crystals: mp 91-92°; ir (CHCI3) 3015, 1405, 1372, 1285, 973, 920, 882, and 874 cm-1; NMR (CDCI3) 3.75 (m, 2 ), 5.1 (m, 2 H), and 6.35 ppm (t, 2 H, J = 4 Hz); mass spectrum m/e (rel. intensity) 126 (10), 95 (8), 94 (100), 81 (7), 68 (11), 66 (42), 65 (7), 64 (metastable), 41 (6), 40 (6).…”

“…A solution of 100 mg of 2 in 2 ml of ethyl acetate was stirred at reflux for 16 hr. The solvent was then evaporated on a rotary evaporator to give 100 mg of white crystals: sublimed at 40°(0.4 Torr); mp 84-86°; ir (CHC13) 3020, 1450, 1239, 950, and 860 cm"1; NMR (CDC13) 3.4 (s, 4), 3.5 ppm (s, 2); NMR (CgDe) 2.4-2.7 (m, 4), 2.8 ppm (s, 2); mass spectrum m/e (rel intensity) 126 (5), 97 (26), 81 (21), 71 (52), 70 (6), 69 (75), 68 (61), 55 (16), 54 (8), 53 (17), 52 (6), 44 (5), 43 A solution of 2 (-20 mg) in ~0.5 ml of CDCI3 was heated at 45°i n an NMR tube. The NMR spectrum was observed at several times during the reaction and from the integration, the percentage conversion to 3 could be derived ¡time (hr), log [2]): 2.1, 1.93; 3.8, 1.90; 7.6, 1.83; 20.8, 1.52; 24.8, 1.42; 32.9, 1.27.…”

cis-[1,2;3,4;5,6]Triiminocyclohexane (cis-benzenetrisimine)

“…(3) (Schwesinger & Prinzbach, 1972;Vogel, Altenbach & Sommerfeld, 1972)]. In the present publication we present the molecular conformation and spatial packing of the title compound (Schwesinger & Prinzbach, 1973). Suitable single crystals were prepared by recrystallization from ethanol under special conditions (Littke, 1974).…”

Chemistry of cis‐Trioxatris‐σ‐homobenzene. Substitutions by Univalent Nucleophiles

“…However, at least partial reaction by way of ( 5 ) cannot be excluded, for it must be remembered that acid hydrolysis of, e.g., the epoxide (5e) from conduri-to1 B affords mainly chiro-inositol ( 6 e ) by way of the e,e,e,e-conformation and only a little scyilo-inositol ( 7 e ) by way of the a,a,a,a-conformati~n'~]. To date we have examined two nucleophilic substitutions of (2). The diazide and the dibromide[81 resulting from the 1,2-attack have structures (4c) and (4 f 1Jattack on ( 2 ) , which is undoubtedly surprising on steric grounds, is favored also by other nucleophiles.…”