FRIEDEL–CRAFTS REARRANGEMENTS IN BRANCHED CONDENSED RING SYSTEMS: I OCTAMETHYLOCTAHYDROANTHRACENE

1961 ◽  
Vol 39 (4) ◽  
pp. 870-880 ◽  
Author(s):  
L. R. C. Barclay ◽  
A. H. Gray ◽  
C. E. Milligan
Keyword(s):  
Double Bond ◽  
Spectral Data ◽  
Aluminum Chloride ◽  
Reduction Product ◽  
Ring Systems ◽  
Olefinic Double Bond

Treatment of 1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydroanthracene (C22H34, I) with aluminum chloride produced a new hydrocarbon (C22H32, II) containing a conjugated olefinic double bond. Hydrocarbon II was proved to be 1,1,5,5,8,8-hexamethyl-3-isopropyl-5,6,7,8-tetrahydrobenzindene by spectral data, by oxidative studies, and by a synthesis of its reduction product, 1,1,5,5,8,8-hexamethyl-3-isopropyl-5,6,7,8-tetrahydrobenzindane (III). A benzenonium ion mechanism is postulated to explain the 1,2-phenyl shift accompanied by dehydrogenation in the formation of II from I. The detection of hydrogen in the off gas of the rearrangement supports this mechanism. A similar benzenonium ion mechanism can be applied to elucidate the mechanism of isomerization of tertiary to secondary alkylbenzenes reported in the literature.

8-Acyl-7-phenylbicyclo[2.2.2]-2,6-diones by rearrangement of 3-acyloxy-5-(2-phenylethenyl)-2-cyclohexen-1-ones. 1H and 13C NMR spectral evidence of their structure

1990 ◽  
Vol 55 (5) ◽  
pp. 1208-1215 ◽  
Author(s):  
Pavel Hrnčiar ◽  
Tibor Liptay ◽  
Ján Šraga
Keyword(s):  
Double Bond ◽  
Spectral Data ◽  
13C Nmr ◽  
1H And 13C Nmr ◽  
Spectral Evidence ◽  
C Nmr

3-Acyloxy-5-(2-phenylethenyl)-2-cyclohexen-1-ones II were prepared by O-acylation of 5-(2-phenylethenyl)-1,3-cycloxanedione (I). Treatment of II with AlCl3 resulted in rearrangement of the acyl group to the double bond of the phenylethenyl grouping followed by cyclization to 8-acyl-7-phenylbicyclo[2.2.2]octane-2,6-diones III. Their structure was evidenced by analysis of the 1H and 13C NMR spectral data.

ChemInform Abstract: Electroreduction of the Activated Olefinic Double Bond in Some 2-Aryl-1(2-acetylamino-1,3,4-thiadiazol-5-yl)-propionitrile Derivatives

ChemInform ◽  
1987 ◽  
Vol 18 (23) ◽  
Author(s):  
M. ABDEL AZZEM ◽  
M. M. M. RAMIZ ◽  
E. A. GHALI ◽  
H. M. FAHMY ◽  
M. R. H. ELMOGHAYAR
Keyword(s):  
Double Bond ◽  
Olefinic Double Bond

Oxydation du cyclohexène par le nitrate cérique d'ammonium

1974 ◽  
Vol 52 (18) ◽  
pp. 3201-3205 ◽  
Author(s):  
Claude Briguet ◽  
Christian Freppel ◽  
Jean-Claude Richer ◽  
Miklos Zador
Keyword(s):  
Double Bond ◽  
Ammonium Nitrate ◽  
Ceric Ammonium Nitrate ◽  
Olefinic Double Bond

The oxidation of cyclohexene by ceric ammonium nitrate has been studied. In anhydrous DMSO the reaction leads to cyclohexene-3-nitrate, while in acetonitrile N-(cyclohexene-2-yl) acetamide is formed. Hydroxylated products are formed in the presence of water. The results obtained are explained in terms of the formation of an intermediate arising from the addition of the radical NO3• to the olefinic double bond. [Journal translation]

Electrochemical Heterodifunctionalization of α-CF3 Alkenes to Access α-Trifluoromethyl-β-sulfonyl Tertiary Alcohols

2021 ◽  
Author(s):  
Zhi-Peng Ye ◽  
Jie Gao ◽  
Xin-Yu Duan ◽  
Jianping Guan ◽  
Fang Liu ◽  
...  
Keyword(s):  
Double Bond ◽  
Hydroxyl Group ◽  
Tertiary Alcohols ◽  
Olefinic Double Bond

An unprecedented electrochemical heterodifunctionalization of α-CF3 alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond...

scholarly journals Synthesis and Biological Evaluation of Furo[3,2-c]pyrazole-5-carbimidates

2019 ◽  
Vol 31 (10) ◽  
pp. 2389-2393
Author(s):  
Sravanthi Siliveri ◽  
Harinadha Babu Vamaraju ◽  
Shivaraj
Keyword(s):  
Antibacterial Activity ◽  
Double Bond ◽  
Spectral Data ◽  
Biological Evaluation ◽  
Significant Protection ◽  
Edema Formation ◽  
Anti Inflammatory ◽  
Alkoxy Groups ◽  
Oxidative Difunctionalization ◽  
Synthesis And Biological Evaluation

In the present work, novel pyrazole fused dihydrofurans synthesized via a chronological addition of N-chloro succinimide and base piperidine to pyrano[3,2-c]pyrazole carbonitrile derivatives in methanol medium. Oxidative difunctionalization was done with the reagent N-chloro succinimide by the addition of both chlorine and alkoxy groups crosswise the chromene double bond. The addition of base results in the construction of dihydrofuran derivatives by ring contraction. The structures of newly synthesized compounds were characterized on the basis of physical and spectral data. Synthesized compounds were evaluated for antibacterial and anti-inflammatory activities. All the compounds exhibited significant antibacterial activity against all the four strains of bacteria and their MICs ranged between 1.56 and 12.55 μg/mL. In anti-inflammatory screening, among all the tested compounds, compounds 7, 8, 9, 11, 12, 13, 14, 16, 17 and 18 exhibited significant protection against the edema formation at a concentration of 100 mg/kg.

Heterometallische Cluster durch ligandunterstützte Metallfragmentkondensation / Heterometallic Clusters by Ligand Assisted Metal Fragment Condensation

1991 ◽  
Vol 46 (9) ◽  
pp. 1169-1176 ◽  
Author(s):  
Wolfgang Rohde ◽  
Gert Fendesak
Keyword(s):  
Double Bond ◽  
Chelate Complexes ◽  
Heterometallic Clusters ◽  
X Ray ◽  
X Ray Crystallography ◽  
Inert Solvent ◽  
Fragment Condensation ◽  
Olefinic Double Bond ◽  
High Yields ◽  
Iron Fragment

Dicobalt complexes of 3-vinylpropargylic alcohol derivatives react with biscyclooctenetricarbonyliron to give new chelate complexes of the iron tricarbonyl fragment with the olefinic double bond and the alcohol oxygen atom bound to the iron fragment. These compounds react upon heating in an inert solvent to give FeCo-alkynyl cluster complexes in high yields. One of these compounds has been structurally characterized by X-ray crystallography.

scholarly journals Coordination of Sodium Cation to an Oxygen Function and Olefinic Double Bond to Form Molecular Adduct Ion in Fast Atom Bombardment Mass Spectrometry

2002 ◽  
Vol 50 (7) ◽  
pp. 935-940 ◽  
Author(s):  
Naoko Morisaki ◽  
Hisayoshi Kobayashi ◽  
Yumiko Yamamura ◽  
Masuo Morisaki ◽  
Kazuo Nagasawa ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Double Bond ◽  
Fast Atom Bombardment ◽  
Sodium Cation ◽  
Molecular Adduct ◽  
Olefinic Double Bond

Group 6 metal carbonyl complexes of tridentate olefinic tertiary diphosphines. Crystal and molecular structure of {(E)-1,3-Bis[2-(diphenylphosphino)phenyl]-propene}tricarbonyltungsten(0),W(CO)3 {(E)-o-Ph2PC6H4CH=CHC6H4PPh2-o}

1980 ◽  
Vol 33 (6) ◽  
pp. 1261 ◽  
Author(s):  
MA Bennett ◽  
S Corlett ◽  
GB Robertson ◽  
WL Steffen
Keyword(s):  
Molecular Structure ◽  
Double Bond ◽  
Crystal And Molecular Structure ◽  
Heavy Atom ◽  
Metal Carbonyl ◽  
Free Ligand ◽  
Spectroscopic Studies ◽  
Carbonyl Complexes ◽  
X Ray Diffraction ◽  
Olefinic Double Bond

The ligands (L) (E)-2,2'-bis(diphenylphosphino)stilbene, (E)-o-Ph2PC6H4CH=CHC6H4PPh2-o (bdps), (E)-1,3-bis[2-(diphenylphosphino)phenyl]propene, (E)-o-Ph2PC6H4CH=CHCH2C6H4PPh2-o (bdpp), and (E)-1,3-bis[2-(diphenylphosphino)phenyl]but-1-ene,( E)-o-Ph2PC6H4CH=CHCHMeC6- H4PPh2-o (bdpb), form complexes of general formula M(CO)3L (M = Cr, Mo, W). N.m.r. (1H, 13C and 31P) and i.r. data indicate that the metal atoms are octahedrally coordinated by mutually trans phosphorus atoms and the double bond of the olefinic tertiary diphosphines and by meridionally disposed carbonyl groups. Conformational isomers of the complexes of bdpb can be detected by n.m.r, spectroscopy, but there is no evidence for similar conformers in the corresponding complexes of bdps and bdpp. The crystal and molecular structure of W(CO)3(bdpp),0.5CH2C12 has been determined by single-crystal X-ray diffraction analysis. The crystals are triclinic, space group PI, with a 10.1 13(Z), b 13.820(2), c 14.512(3) A, α 76.24(1), β 88.08(1), γ 76.31(1)°. The structure, solved by the heavy-atom method and refined to a conventional R of 0.049 for 8418 diffractometer data, confirms the conclusions drawn from spectroscopic studies. The olefinic double bond of bdpp is attached symmetrically to the metal atom [W-C(olefin) 2.403(8), 2.387(9) Ǻ] and is roughly parallel to the P-W-P axis. The C=C bond length of 1.359(11) Ǻ is only slightly longer than that expected for the free ligand and is indicative of relatively weak metal-olefin back-bonding. Other important bond lengths are: W-P 2.450(2), 2.462(2) Ǻ and W-C(C0) 2.020(7), 2.024(7) Ǻ (CO trans to CO) and 1.971(7) Ǻ (CO trans to olefin).

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