Crystal and molecular structure of 1,4-epoxy-4-(4-nitrophenylmethyl)-1-phenyl-1H-2,3-benzodioxepin-5(4H)-one

Abstract

Crystal and Molecular Structure of I ,4-Epoxy-4-(4-nit rophenylmethyl ) - I -phenyl-1 H-2,3benzodioxepin-5(4H)-one

Acid-catalyzed cyclization of 3,3',4,4'-tetrahydro-1,1'-binaphthyl and single-crystal x-ray structure determination of a polycyclic stable ozonide

“…the blue color changed to yellow. The yellow solid that remained after solvent removal was recrystallized from chloroform-acetone to give 300 mg (67%) of the bis-TCNE adduct 16: mp 160 °C dec; XH NMR (250 MHz, acetone-d6) 5 7.79 (s, 2 H), 6.62 (d, J = 1.9 Hz, 2 H), 6.30 (d, J = 1.9 Hz, 2 H); 13C NMR (20 MHz, acetone-d6) 5 151.09,144.90,133.95,121.38,120.30,120.11, 73.17, 71.20, 61.94, 61.80; IR (KBr) 3010 (m), 2940 (w), 2260 (w), 1500 (w), 810 cm'1 (s); mass spectrum, m/e (relative intensity) 190 (100), 158 (4), 145 (14), 128 (57). Anal.…”

“…When the ozonization experiment was repeated using 10% methanol/methylene chloride solution as the solvent, the same product was obtained in comparable yields: IR (KBr) 1258,1124 (C-0 stretch) cm"1; mass spectrum (70 eV), mjz (relative intensity) 306 (M+-, 10.7), 274 (100), 273 (50.0), 272 (72.6), 271 (68.4), 256 (62.1); !H NMR (CDC13) $ 7.9-7.72 (m, 1 H, Ar H), 7.42-6.94 (m, 6 H, Ar H), 2.25 and 3.23 (dd, 1 H, C-12c), 3.2-3.74 (m, 4 H, Ar CH), 2.5-1.8 (m, 6 H, CH2); 13C NMR (CDC13) ppm 139.6,135.5, 135.1, 131.1, 130.6, 129.7, 128.2, 128.1, 126.7, 107.3, 105.0, 44.8, 30.3, 29.4, 28.5, 28.5, 20.7.…”

“…Recrystallization from 95% ethanol gave yellow crystals, mp 139-140 °C. These crystals were sublimed at 120 °C (0.05 mm) to give 5: mp 140.5-141 °C; UV (95% ethanol) Iw 274 nm (log c 4.84); mass spectrum (9 eV), m/z (relative intensity) 257 (22.3), 256 (M+-, 100), 255 (25.3), 252 (22.3), 228 (65.9); NMR h 7.0-8.1 (m, 8 H, Ar H), 3.69 (dd, 1 H, CH(Ar)3), 2.6-3.2 (m, 3 H, overlapping), 2.04-2.4 (m, 2 H, overlapping), 1.04-1.52 (m, 1 H, overlapping); 13C NMR (CDC13) 6 Anal. Calcd for C20H16: C, 93.71; H, 6.29.…”

“…Calcd for C20H16: C, 93.71; H, 6.29. Found: C, 93.62; H, 6.31. Dehydrogenation of 2a to BenzoLf]fluoranthene (6). In a 100-mL, round-bottomed flask equipped with a magnetic stirrer, condenser, and argon purge were combined 500 mg (2.0 mmol) of alkene 2a, 100 mg of 10% Pd/C, and 50 mL of 1-methylnaphthalene.…”

Ethyl 1-ethyl-7-methoxy-3,4-dioxo-2-phenanthrenecarboxylate, C20H18O5

“…Reduction of the ozonide by hydrogen and platinum(IV) oxide led to the formation of the title compound (Hwang, 1962). The first two complete single-crystal crystallographic investigations of stable ozonides were carried out recently (Oliver, Mullica, Milligan, Karban, McAtee & Belew, 1979;Mullica, Korp, Milligan, Belew, McAtee & Karban, 1979). Our keen interest in ozonides and compounds which may serve as intermediates in the preparation of steroids has propagated the structural analysis of the title compound.…”