Petrenko-Kritschenko Piperidone Synthesis
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Petrenko-Kritschenko Piperidone Synthesis
The Petrenko-Kritschenko reaction is a classic multicomponent-name reactionJie-Jack Li; "Name reactions in heterocyclic chemistry"; 2005 John Wiley & Sons; ; pp313 that is closely related to the Robinson–Schöpf tropinone synthesis, but was published 12 years earlier. Classic reaction In the original publicationP. Petrenko-Kritschenko "Über die Kondensation des Acetondicarbonsäureesters mit Aldehyden, Ammoniak und Aminen" Journal für Praktische Chemie Volume 85, Issue 1, pages 1–37, 20 May 1912; diethyl-α-ketoglurate, a derivative of acetonedicarboxylic acid, is used in combination with ammonia and benzaldehyde. The relative stereochemistry was not elucidated in the original publication, structural analysis using X-rays or NMR was not available in these days. In the absence of ammonia or ammonium salts a 4-oxotetrahydropyran is formed.P. Petrenko-Kritschenko "Über Tetrahydropyronverbindungen" Journal für Praktische Chemie; Volume 60, Issue 1, pages 140–158, 27 December ...
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Paul Petrenko-Kritschenko
Paul may refer to: *Paul (given name), a given name (includes a list of people with that name) *Paul (surname), a list of people People Christianity *Paul the Apostle (AD c.5–c.64/65), also known as Saul of Tarsus or Saint Paul, early Christian missionary and writer *Pope Paul (other), multiple Popes of the Roman Catholic Church *Saint Paul (other), multiple other people and locations named "Saint Paul" Roman and Byzantine empire *Lucius Aemilius Paullus Macedonicus (c. 229 BC – 160 BC), Roman general *Julius Paulus Prudentissimus (), Roman jurist *Paulus Catena (died 362), Roman notary *Paulus Alexandrinus (4th century), Hellenistic astrologer *Paul of Aegina or Paulus Aegineta (625–690), Greek surgeon Royals *Paul I of Russia (1754–1801), Tsar of Russia *Paul of Greece (1901–1964), King of Greece Other people *Paul the Deacon or Paulus Diaconus (c. 720 – c. 799), Italian Benedictine monk *Paul (father of Maurice), the father of Maurice, Byzan ...
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Pseudopelletierine
Pseudopelletierine is the main alkaloid derived from the root-bark of the pomegranate tree (''Punica granatum''), along with at least three other alkaloids: pelletierine, isopelletierine, and methylpelletierine (C9H17ON), which yield 1.8, 0.52, 0.01, and 0.20 grams per kilogram of raw bark. It is a homolog of tropinone, and can be synthesized in a manner analogous to the classical Robinson tropinone synthesis, using glutaraldehyde (rather than succinaldehyde), acetonedicarboxylic acid, and methylammonium chloride. It was the starting material for Willstätter's 10-step synthesis of cyclooctatetraene 1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of ..., which was achieved after oxidation and several Hoffman elimination steps. References Alkaloids Ketones Nitrogen heterocy ...
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Hydrogen Peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%–6% by weight) in water for consumer use, and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or " high-test peroxide", decomposes explosively when heated and has been used as a propellant in rocketry. Hydrogen peroxide is a reactive oxygen species and the simplest peroxide, a compound having an oxygen–oxygen single bond. It decomposes slowly when exposed to light, and rapidly in the presence of organic or reactive compounds. It is typically stored with a stabilizer in a weakly acidic solution in a dark bottle to block light. Hydrogen peroxide is found in biological systems including the human body. Enzymes that use or decompose hydrogen peroxide are classified as peroxidases. Properties The boiling poi ...
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Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon. Cyclohexyl () is the alkyl substituent of cyclohexane and is abbreviated Cy. Production Modern On an industrial scale, cyclohexane is produced by hydrogenation of benzene in the presence of a Raney nickel catalyst. Producers of cyclohexane account for approximately 11.4% of global demand for benzene. The reaction is highly exothermic, with ΔH(500 K) = -216.37 kJ/mol. Dehydrogenation commenced noticeably above 300 °C, reflecting the favorable entropy for dehydrogenation. : Early Unlike benzene, cyclohexane is not found in natural resources such as coal. For this reason, early investigators synthesized their cyclohexane ...
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High-valent Iron
High-valent iron commonly denotes compounds and intermediates in which iron is found in a formal oxidation state > 3 that show a number of bonds > 6 with a coordination number ≤ 6. The term is rather uncommon for hepta-coordinate compounds of iron. It has to be distinguished from the terms hypervalent and hypercoordinate, as high-valent iron compounds neither necessarily violate the 18-electron rule nor necessarily show coordination numbers > 6. The ferrate(VI) ion eO4sup>2− was the first structure in this class synthesized. The synthetic compounds discussed below contain highly oxidized iron in general, as the concepts are closely related. Oxoiron compounds Oxoferryl species are commonly proposed as intermediates in catalytic cycles, especially biological systems in which O2 activation is required. Diatomic oxygen has a high reduction potential (E0 = 1.23 V), but the first step required to harness this potential is a thermodynamically unfavorable one electron reduction E0 = ...
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Coccinellidae
Coccinellidae () is a widespread family of small beetles ranging in size from . They are commonly known as ladybugs in North America and ladybirds in Great Britain. Some entomologists prefer the names ladybird beetles or lady beetles as they are not true bugs. Many of the species have conspicuous aposematic colours and patterns, such as red with black spots, that warn potential predators that they are distasteful. The majority of the more than 6,000 described species are generally considered beneficial insects, because many prey on herbivorous hemipterans such as aphids or scale insects, which are agricultural pests. Many coccinellids lay their eggs directly in aphid and scale insect colonies, ensuring their larvae have an immediate food source. However, some species such as the herbivorous Mexican bean beetle are agricultural pests. Etymology The name ''coccinellids'', created by Pierre André Latreille, is derived from the Latin word ''coccineus'' meaning "scarlet". The na ...
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Indium
Indium is a chemical element with the symbol In and atomic number 49. Indium is the softest metal that is not an alkali metal. It is a silvery-white metal that resembles tin in appearance. It is a post-transition metal that makes up 0.21 parts per million of the Earth's crust. Indium has a melting point higher than sodium and gallium, but lower than lithium and tin. Chemically, indium is similar to gallium and thallium, and it is largely intermediate between the two in terms of its properties. Indium was discovered in 1863 by Ferdinand Reich and Hieronymous Theodor Richter by spectroscopic methods. They named it for the indigo blue line in its spectrum. Indium was isolated the next year. Indium is a minor component in zinc sulfide ores and is produced as a byproduct of zinc refinement. It is most notably used in the semiconductor industry, in low-melting-point metal alloys such as solders, in soft-metal high-vacuum seals, and in the production of transparent conductive coati ...
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Chromium Trioxide
Chromium trioxide (also known as chromium(VI) oxide or chromic anhydride) is an inorganic compound with the formula CrO3. It is the acidic anhydride of chromic acid, and is sometimes marketed under the same name. This compound is a dark-purple solid under anhydrous conditions, bright orange when wet and which dissolves in water concomitant with hydrolysis. Millions of kilograms are produced annually, mainly for electroplating. Chromium trioxide is a powerful oxidiser and a carcinogen. Production, structure, and basic reactions Chromium trioxide is generated by treating sodium dichromate with sulfuric acid: :H2SO4 + Na2Cr2O7 → 2 CrO3 + Na2SO4 + H2O Approximately 100,000 tonnes are produced annually by this or similar routes. The solid consists of chains of tetrahedrally coordinated chromium atoms that share vertices. Each chromium center therefore shares two oxygen centers with neighbors. Two oxygen atoms are not shared, giving an overall stoichiometry of 1:3. : The s ...
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