The preparation and rearrangement of some 2,3-oxygenated 2-phenylbornanes

1971 ◽  
Vol 24 (5) ◽  
pp. 1009 ◽  
Author(s):  
JM Coxon ◽  
MP Hartshorn ◽  
AJ Lewis
Keyword(s):  
Thionyl Chloride ◽  
Major Product ◽  
Similar Reaction ◽  
Unsaturated Aldehyde

Reaction of the r-2-hydroxy-2-phenyl-c-3-p-tolylsulphonyloxybornanes (4b) and (10b) with base gave the epimeric 2,3-epoxy-2-phenylbornanes (1) and (2). Acid-catalysed rearrangement of the endo-epoxide (2) gave 2-endo-phenylbornan-3-one (8); similar reaction of the exo-epoxide (1) afforded the unsaturated aldehyde (6) as the major product. Pyrolysis of the cyclic sulphites (16) and (17), prepared from the 2,3-exo-diol (4a) by reaction with thionyl chloride, gave mixtures of 2-endo- phenylbornan-3-one (8) and the aldehyde (5).

Halides and oxide halides of technetium. I. Technetium(V) oxide halides and the reaction of thionyl chloride with ammonium pertechnetate

1968 ◽  
Vol 21 (8) ◽  
pp. 1981 ◽  
Author(s):  
R Colton ◽  
IB Tomkins
Keyword(s):  
Thionyl Chloride ◽  
Major Product ◽  
Chloride Adduct

Chlorination of technetium dioxide has been shown to give technetium oxide trichloride as the major product. The presence of an unstable second product, thought to be the oxide tetrachloride, was confirmed. Bromination of technetium dioxide gives only technetium oxide tribromide. Thionyl chloride reacts with ammonium pertechnetate to give ammonium dioxotetrachlorotechnetate(V1), which was isolated as its sulphuryl chloride adduct, (NH4),[TcO2Cl4],SO2Cl2.

Synthesis of new substituted dihydroheptalene derivatives: SiO2- and base-catalyzed rearrangement of dimethyl trans-3,8-dihydroheptalene-3,8-dicarboxylate

2001 ◽  
Vol 79 (1) ◽  
pp. 35-41
Author(s):  
Nurullah Saraçoglu ◽  
Abdullah Menzek ◽  
Armagan Kinal ◽  
Metin Balci
Keyword(s):  
Room Temperature ◽  
Heat Of Formation ◽  
Major Product ◽  
Similar Reaction ◽  
Am1 Calculations ◽  
Hydrogen Shift ◽  
Proton Shift ◽  
Major Isomer ◽  
Prolonged Reaction Time ◽  
Lower Heat

Dimethyl trans-3,8-dihydroheptalene-3,8-dicarboxylate (trans-3) isomerizes to dimethyl cis-3,8-dihydroheptalene-3,8-dicarboxylate (cis-3) upon treatment with SiO2. On the other hand, base-catalyzed reaction of trans-3 undergoes a direct 1,3-intramolecular proton shift to give 6 at room temperature in 5 min. Prolonged reaction time formed isomers 7 and 8 in a ratio of 4:1. AM1 calculations indicate that the isomer 8, which is formed as minor product, has a lower heat of formation (–99.34 kcal mol–1) than that of the major isomer 7 (–92.05 kcal mol–1). However, when a similar reaction was performed at 100°C, the thermodynamically more stable isomer 8 was formed as the major product. Furthermore, cycloaddition reactions of these new dihydroheptalene derivatives 6 and 7 with different dienophiles have been studied. The mechanism has been discussed.Key words: dihydroheptalene, cycloaddition, 1,3-hydrogen shift, cycloheptatriene–norcaradiene equilibrium.

Preparation of antidotes for anticholinesterase poisoning. IV. Synthesis and protective effectiveness of 2′-(cis- and trans-2″-hydroxycyclohexyl)aminoethyl 1-phenylcyclopentanecarboxylate hydrochlorides

1970 ◽  
Vol 48 (9) ◽  
pp. 1377-1382 ◽  
Author(s):  
R. A. B. Bannard ◽  
J. H. Parkkari
Keyword(s):  
Thionyl Chloride ◽  
Similar Reaction ◽  
Cis And Trans ◽  
Hydrolysis Of ◽  
Protective Effectiveness

The syntheses of cis- and trans-2-aminocyclohexanols and of cis- and trans-2-ethylaminocyclohexanols are described. The cis isomers were prepared by treatment of the corresponding trans-2-acetamidocyclohexanols with thionyl chloride followed by hydrolysis of the resulting intermediate oxazolines. The 2-aminocyclohexanols were converted to 2′-(cis- and trans-2″-hydroxycyclohexyl)aminoethyl 1-phenyl-cyclopentanecarboxylate hydrochlorides (1 and 2, R = H) by treatment with 2′-bromoethyl 1-phenyl-cyclopentanecarboxylate, but attempts to convert the 2-ethylaminocyclohexanols to 1 and 2 (R = C2H5) by a similar reaction were unsuccessful. The anticholinesterase activities of several of the compounds are discussed, as are the potencies of 1 and 2 (R = H) in protecting mice and rats from sarin poisoning.

Acetylenic Acids. IV. The Reactions of Alkoxy-Substituted Phenylpropiolic Acids and Esters with Sulfur Halides, Particularly Thionyl Chloride

1979 ◽  
Vol 32 (4) ◽  
pp. 833 ◽  
Author(s):  
CM Bonnin ◽  
PA Cadby ◽  
CG Freeman ◽  
AD Ward
Keyword(s):  
Thionyl Chloride ◽  
Major Product ◽  
Sulfur Monochloride ◽  
Sulfur Dichloride ◽  
Substituted 1 ◽  
Acetylenic Acids

3,4-Dialkoxy-substituted phenylpropiolic acids and esters react with thionyl chloride to give good yields of substituted 1-benzothiophen systems. Similar reactions of m-and p-methoxyphenylpropiolic acids and 3,4,5-trimethoxyphenylpropiolic acid, which yield mixtures of products, are reported. In contrast, 2,5- and 2,3-dimethoxyphenylpropiolic acids gave mixtures in which a coumarin is the major product. The effect of adding pyridine to the reaction mixture is outlined. Reactions involving sulfur monochloride and sulfur dichloride generally gave much lower yields of these products. Attempts to form organometallic intermediates from the 3-chloro-1-benzothiophen products were unsuccessful.

Novel Rearrangements of the 2-Chloroacrylonitrile Cycloadducts of Steroidal 14,16-Dien-17-yl Acetates

2001 ◽  
Vol 66 (12) ◽  
pp. 1777-1796 ◽  
Author(s):  
James R. Bull ◽  
Richard S. Gordon ◽  
Claudia Grundler
Keyword(s):  
Functional Group ◽  
Major Product ◽  
Similar Reaction ◽  
Rearrangement Product ◽  
Methyl Derivative ◽  
Bond Scission ◽  
Grob Fragmentation

Cycloaddition of 3-methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate (1) with 2-chloroacrylonitrile furnishes 17β-acetoxy-16α-chloro-3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-16β-carbonitrile (2) as the major product, which undergoes alkali-mediated rearrangement to (161R)-3-methoxy-17-oxo-16β,15β,14-(ethane[1,1,2]triyl)-14β-estra-1,3,5(10)-triene-161-carbonitrile (7). A similar reaction course is followed by the related 16-methyl derivative 4, and it is shown that minor 15-chloro-15-cyano cycloadducts 3 and 6 undergo Grob fragmentation. Functional group manipulations and regioselective bond-scission processes are described, for conversion of rearrangement product 7 into 16β,15β,14-(ethane[1,1,2]triyl) and cyclobuta[14β,15β] analogues of estradiol.

METABOLISM OF 17α-HYDROXYPROGESTERONE-4-14C-17α-CAPROATE BY HOMOGENATES OF RAT LIVER AND HUMAN PLACENTA

1961 ◽  
Vol 36 (4) ◽  
pp. 511-519 ◽  
Author(s):  
Margaret Wiener ◽  
Charles I. Lupa ◽  
E. Jürgen Plotz
Keyword(s):  
Rat Liver ◽  
Human Placenta ◽  
Steric Hindrance ◽  
Placental Tissue ◽  
Caproic Acid ◽  
Major Product ◽  
Side Chain ◽  
Anaerobic Conditions ◽  
Prolonged Action ◽  
Long Acting

ABSTRACT 17α-hydroxyprogesterone-4-14C-17α-caproate (HPC), a long-acting progestational agent, was incubated with homogenates of rat liver and human placenta. The rat liver was found to reduce Ring A of HPC under anaerobic conditions to form allopregnane-3β,17α-diol-20-one-17α-caproate and pregnane-3β,17α-diol-20-one-17α-caproate, the allopregnane isomer being the major product. The caproic acid ester was neither removed nor altered during the incubation. Placental tissue did not attack HPC under conditions where the 20-ketone of progesterone was reduced. It is postulated that this absence of attack on the side chain is due to steric hindrance from the caproate ester, and that this may account for the prolonged action of HPC.

Flavor Profile Analysis and GC/MS Detection of Phenolic Iodinated Disenfection Byproducts in Drinking Water for the USA Space Program

1999 ◽  
Vol 40 (6) ◽  
pp. 45-51 ◽  
Author(s):  
Andrea M. Dietrich ◽  
Susan Mirlohi ◽  
Willian F. DaCosta ◽  
Jennifer Peters Dodd ◽  
Richard Sauer ◽  
...  
Keyword(s):  
Drinking Water ◽  
Potable Water ◽  
Profile Analysis ◽  
Major Product ◽  
Space Program ◽  
Odor Threshold ◽  
Odor Evaluation ◽  
The Usa ◽  
Flavor Profile Analysis ◽  
Flavor Profile

Reactions of iodine and phenol were investigated to determine which iodophenols were produced and their odor properties. The research was performed in support of the USA space program that applies iodine to disinfect potable water for spacecraft use. Higher concentrations (50 mg/l) and higher iodine:phenol (e.g. 10:1) ratios resulted in the formation of greater iodophenol concentrations and higher substituted iodophenols. The reactions were fast and nearly complete within 1 hour. For pH 5.5 and 8 and all iodine:phenol ratios, formation of monosubstituted compounds indicated that 2-iodophenol was favored over 4-iodophenol. At the intermediate iodine:phenol ratios of 1:1 and 2:1, substantial amounts of the diiophenols formed and persisted for up to 32 days. The diiodophenols were not detected at iodine:phenol ratios of 0.2:1 and 10:1. The compound 2,4,6-triiodophenol was the major product formed at a 10:1 iodine:phenol ratio and the formation of this trisubstituted phenol appeared nearly complete. Odor evaluation indicated that the iodophenols have much lower odor threshold concentrations (OTC) than phenol. The 2- and 4- iodophenol had OTC values of ≅ 1 and 500 μg/l, respectively, with odors described as “medicinal, phenol, chemical”.

Safety of a Clozapine Trial Following Quetiapine-Induced Leukopenia: A Case Report

2019 ◽  
Vol 14 (1) ◽  
pp. 80-83 ◽  
Author(s):  
Asma H. Almaghrebi
Keyword(s):  
Treatment Options ◽  
Young Female ◽  
Similar Reaction ◽  
Careful Monitoring ◽  
Treatment Resistant ◽  
Blood Cell Count ◽  
Antipsychotic Medications ◽  
Case Presentation ◽  
Clozapine Treatment ◽  
History Of

Background: The clozapine-derivative quetiapine has been shown in some cases to cause leukopenia and neutropenia. Case Presentation: We reported on a case of a young female diagnosed with treatment-resistant schizophrenia. After failed trials of three antipsychotic medications and despite a history of quetiapineinduced leukopenia, clozapine treatment was introduced due to the severity of the patient’s symptoms, the limited effective treatment options, and a lack of guidelines on this issue. Result: Over a ten-week period of clozapine treatment at 700 mg per day, the patient developed agranulocytosis. Her white blood cell count sharply dropped to 1.6 &#215; 10<sup>9</sup> L, and her neutrophils decreased to 0.1 &#215; 10<sup>9</sup> L. There had been no similar reaction to her previous medications (carbamazepine, risperidone, and haloperidol). Conclusion: The safety of clozapine in a patient who has previously experienced leukopenia and neutropenia with quetiapine requires further investigation. Increased attention should be paid to such cases. Careful monitoring and slow titration are advisable.

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