chembox Reference ref http www.sigmaaldrich.com catalog search ProductDetail ALDRICH 125482 cis Cyclooctene at Sigma Aldrich ref Name cis small top small and trans Cyclooctene ImageFile Cycooctene Isomers Structural Formulae.png ImageSize 200px IUPACName E Cyclooctene br Z Cyclooctene OtherNames cis Cyclooctene br trans Cyclooctene Section1 Chembox Identifiers ChemSpiderID 553642 InChI 1 C8H14 c1 2 4 6 8 7 5 3 1 h1 2H,3 8H2 b2 1 InChIKey URYYVOIYTNXXBN UPHRSURJBT CASNo 931 87 3 PubChem 638079 SMILES C 1 C CCCCCC 1 Section2 Chembox Properties C 8 H 14 Appearance Density 0.846 g mL MeltingPtC 16 BoilingPt 145 146 C Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Cyclooctene is a cycloalkene with an eight membered ring. It is notable because it is the smallest cycloalkene that can exist as either the cis trans isomerism cis or trans isomer with the cis isomer more common. Its most stable cis stereoisomer can adopt various conformations, the most stable one being shaped like a ribbon ref Ulrich Neuenschwander, Ive Hermans http pubs.acs.org doi full 10.1021 jo202176j cis Cyclooctene , J. Org. Chem. , Vol. 76, p.10236 2011 ref its most stable trans conformer is shaped like the 8 carbon equivalent chair conformation of cyclohexane. class wikitable Image Cis cyclooctene3D.png 150px align right Image Trans cyclooctene3D.png 150px align center cis Cyclooctene ... left trans Cyclooctene trans Cyclooctene is the smallest cycloalkene in which the trans isomer is stable .... trans Cyclooctene exists in a helical conformation with the carbon chain lying above the double bond on one side and below it on the other, leading to chirality as depicted to the right . trans Cyclooctene ... www.orgsyn.org orgsyn orgsyn prepContent.asp?prep CV5P0315 trans Cyclooctene , Organic Syntheses ... in just one step Image Trans cyclooctene synthesis.svg 400px Photochemical trans cyclooctene synthesis Royzen 2008 Although the cis trans equilibrium is unfavorable, the reaction can ... more details
DISPLAYTITLE C sub 8 sub H sub 14 sub The molecular formula C sub 8 sub H sub 14 sub molar mass 110.20 g mol may refer to Cyclooctene Bicyclo 2.2.2 octane Bicyclo 2.2.2 octane Bicyclo 3.3.0 octane Bicyclo 3.3.0 octane 3 methylbicyclo 2.2.1 heptane 3 methylbicyclo 2.2.1 heptane Methylenecycloheptane 2,2 dimethyl 3 hexyne Biisobutenyl Allylcyclopentane Octyne Methylcycloheptene Bimethallyl MolFormDisambig ... more details
Hofmann elimination also known as exhaustive methylation or the Hofmann Degradation is a process where an amine is reacted to create a tertiary amine and an alkene by treatment with excess methyl iodide followed by treatment with silver oxide , water , and heat. ref JerryMarch ref Image HofmannElimination.svg Hofmann elimination After the first step, a quaternary ammonium quaternary ammonium iodide salt is created. After replacement of iodine by an hydroxyl anion, an elimination reaction takes place to the alkene. With unsymmetrical amines, the major alkene product is the least substituted and generally the least stable, an observation known as the Hofmann rule . This is in direct contrast to normal elimination reactions where the more substituted, stable product is dominant Zaitsev s rule . The reaction is named after its discoverer August Wilhelm von Hofmann . ref Beitr ge zur Kenntniss der fl chtigen organischen Basen Annalen der Chemie und Pharmacie Volume 78, Issue 3, Date 1851 , Pages 253 286 Aug. Wilh. von Hofmann DOI 10.1002 jlac.18510780302 ref An example is the synthesis of trans cyclooctene ref Organic Syntheses , Coll. Vol. 5, p.315 1973 Vol. 49, p.39 1969 .http www.orgsynth.org orgsyn pdfs CV5P0315.pdf ref Image Trans cycloocteneSynthesis.svg Trans cyclooctene Synthesis In a related chemical test called Herzig Meyer alkimide group determination a tertiary amine with at least one methyl group and lacking a beta proton is allowed to react with hydrogen iodide to the quaternary ammonium salt which when heated degrades to iodomethane and the secondary amine. ref Ueber den Nachweis und die Bestimmung des am Stickstoff gebundenen Alkyls p 319 320 J. Herzig, H. Meyer Berichte der deutschen chemischen Gesellschaft Volume 27, Issue 1 , Pages 319 320 1894 DOI 10.1002 cber.18940270163 ref See also The Hofmann rearrangement or Hofmann degradation The Emde degradation . References Reflist DEFAULTSORT Hofmann Elimination Category Elimination reactions Category Name r ... more details
Image Cyclopropane.png thumb 150px right Cyclopropane is the smallest alicyclic compound. An alicyclic compound is an organic compound that is both Aliphatic compound aliphatic and cyclic compound cyclic . They contain one or more all carbon rings which may be either saturation chemistry saturated or unsaturated, but do not have aromaticity aromatic character. ref GoldBookRef title Alicyclic compounds file A00216 year 1995 ref Alicyclic compounds may or may not have aliphatic side chains attached. The simplest alicyclic compounds are the monocyclic cycloalkane s cyclopropane , cyclobutane , cyclopentane , cyclohexane , cycloheptane , cyclooctane , cyclononane , cyclodecane , cycloundecane , cyclododecane , and so on. Bicyclic molecule Bicyclic alkanes include bicycloundecane and decalin . Polycyclic compound Polycyclic alkanes include cubane , basketane , and housane . Spiro compound s have two or more rings that are connected through only one carbon atom. An exocyclic group is always shown outside the ring structure, take for instance the exocyclic double bond on the left Image Exocyclic.png 200px Left exocyclic double bond Right regular double bond br style clear both See for an example isotoluene . The placement of double bonds in many alicyclic compounds can be predicted with Bredt s rule . The mode of ring closing in the formation of many alicyclic compounds can be predicted by Baldwin s rules . Cycloalkenes Image Cyclohexene.png thumb right Cyclohexene is an alicyclic compound with a double bond. Monocyclic cycloalkene s are cyclopropene , cyclobutene , cyclopentene , cyclohexene , cycloheptene , cyclooctene , and so on. Bicyclic alkenes include norbornene and norbornadiene . References references Category Organic compounds Category Organic chemistry ar ca Compost alic clic de Alicyclische Verbindungen et Alits klilised hendid el fa fr Compos alicyclique he hu Aliciklusos vegy let ... more details
The Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the aid of sulfuric acid . ref cite journal title The Preparation of Ethylene Imine from Monoethanolamine author Henry Wenker journal Journal of the American Chemical Society year 1935 volume 57 issue 1 pages 2328 2328 doi 10.1021 ja01314a504 ref Image WenkerSynthesis.png center 500px Wenker synthesis The original Wenker synthesis of aziridine itself takes place in two steps. In the first step ethanolamine is reacted with sulfuric acid at high temperatures 250 C to the sulfonate salt, This salt is then reacted with sodium hydroxide in the second step forming aziridine. The base chemistry base abstracts an amine proton enabling it to nucleophilic displacement displace the sulfonate group. A modification of this reaction involving lower reaction temperatures 140 180 C and therefore reduced charring increases the yield of the intermediate. ref A Modification of Wenker s Method of Preparing Ethyleneimine Philip A. Leighton, William A. Perkins, and Melvin L. Renquist J. Am. Chem. Soc. 1947 69 6 pp 1540 1540. DOI 10.1021 ja01198a512 ref Starting from epoxide cyclooctene oxide , trans 2 Aminocyclooctanol gives a mixture of Cyclo ctenimine and of cyclooctanone as a result of competing Hofmann elimination . ref Chemistry of Ethylenimine. VII. Cyclo ctenimine or 9 Azabicyclo 6.1.0 nonane D. V. Kashelikar, Paul E. Fanta J. Am. Chem. Soc. 1960 82 18 4927 4930. DOI 10.1021 ja01503a044 ref Image WenkerSynthApplic.png center 500px 9 Azabicyclo 6.1.0 nonane synthesis References Reflist DEFAULTSORT Wenker Synthesis Category Substitution reactions Category Name reactions de Wenker Synthese zh Wenker es S ntesis de Wenker ... more details
Other uses Dechlorane disambiguation Dechlorane Chembox ImageFile Dechlorane plus.png ImageSize 200px IUPACName 1,2,3,4,7,8,9,10,13,13,14,14 dodecachloro 1,4,4a,5,6,6a,7,10,10a,11,12,12a dodecahydro 1,4,7,10 dimethanodibenzo a , e cyclooctene OtherNames Dechloran A Section1 Chembox Identifiers ChemSpiderID 24323 InChI 1 C18H12Cl12 c19 9 10 20 15 25 7 3 4 8 6 2 1 5 7 13 9,23 17 15,27 28 14 24 11 21 12 22 16 8,26 18 14,29 30 h5 8H,1 4H2 InChIKey UGQQAJOWXNCOPY UHFFFAOYAP CASNo 13560 89 9 EINECS 236 948 9 PubChem 26111 SMILES Cl C2 C Cl C3 Cl C1CCC4C CCC1C2 Cl C3 Cl Cl C5 Cl C Cl C Cl C4 Cl C5 Cl Cl Section2 Chembox Properties Formula C sub 18 sub H sub 12 sub Cl sub 12 sub MolarMass 653.72 g mol Appearance white, crystalline solid Density 1.8 g cm sup 3 sup MeltingPt 350 C decomp BoilingPt Solubility 0.044 249 g L Section3 Chembox Hazards MainHazards FlashPt Autoignition Dechlorane plus is a organochlorine polychlorinated flame retardant produced by Oxychem . Its Partition coefficient LogP is 9.3. It is produced by the Diels Alder reaction of two equivalents of hexachlorocyclopentadiene with one equivalent of cyclooctadiene . References cite web url http www.epa.gov HPV pubs summaries dechlorp c15635.pdf title Dechlorane Plus High Production Volume HPV Chemical Challenge Program Test Plan. 201 15635. last ENVIRON Health Sciences Institute date August 2004 accessdate 2009 03 20 DEFAULTSORT Dechlorane Plus Category Organochlorides Category Persistent organic pollutants organohalide stub ... more details
chembox verifiedrevid 409798804 ImageFile benzylideneacetone iron tricarbonyl 2D skeletal.png ImageFile1 benzylideneacetone iron tricarbonyl 3D balls.png IUPACName OtherNames Section1 Chembox Identifiers CASNo 38333 35 6 PubChem SMILES Section2 Chembox Properties Formula C sub 13 sub H sub 10 sub FeO sub 4 sub MolarMass 286.060 Appearance Density MeltingPt 88 89 C BoilingPt Solubility Section7 Chembox Hazards MainHazards FlashPt Autoignition The organometallic compound benzylideneacetone iron tricarbonyl is a widely employed reagent for transferring the Fe CO sub 3 sub unit to other organic molecules. ref Kn lker, H. J. sup 4 sup Benzylideneacetone tricarbonyliron in Encyclopedia of Reagents for Organic Synthesis Ed L. Paquette 2004, J. Wiley & Sons, New York. doi 10.1002 047084289 . ref This red colored compound is commonly abbreviated bda Fe CO sub 3 sub . It is prepared by the reaction of diiron nonacarbonyl Fe sub 2 sub CO sub 9 sub with benzylideneacetone , typically in refluxing diethyl ether . ref Alcock, N. W. Richards, C. J. Thomas, S. E. Preparation of Tricarbonyl sup 4 sup vinylketene iron 0 Complexes from Tricarbonyl sup 4 sup vinyl ketone iron 0 Complexes and Their Subsequent Conversion to Tricarbonyl sup 4 sup vinylketenimine iron 0 Complexes Organometallics 1991, volume 10, pp 231 238. doi 10.1021 om00047a054 . ref The identity and purity of the compound can be determined by its IR spectroscopy IR spectrum it absorbs strongly at 2065, 2005, and 1985 wavenumber cm sup 1 sup in cyclohexane solution. Related Fe CO sub 3 sub transfer agents A popular source of Fe CO sub 3 sub is the simplest, Fe sub 2 sub CO sub 9 sub . Alternatively, Fe CO sub 3 sub cyclooctene sub 2 sub is highly reactive, the trade off being that it is thermally sensitive. Imine derivatives of cinnamaldehyde , e.g. C sub 6 sub H sub 5 sub CH CHC H NC sub 6 sub H sub 5 sub , form conveniently reactive Fe CO sub 3 sub adduct s, which have been shown to be superior in some ways to ... more details
Planar chirality is the special case of Chirality mathematics chirality for two dimension s. Most fundamentally, planar Chirality mathematics chirality is a Mathematics mathematical term, finding use in chemistry , physics and related physical sciences, for example, in astronomy , optics and metamaterials . Recent occurrences in latter two fields are dominated by microwave applications and micro and nanostructure d planar interfaces for visible and infrared light . Planar chirality in chemistry Image Planar chiral ferrocene derivative.PNG thumb right An planar chiral derivative of ferrocene , used for kinetic resolution of some racemic secondary alcohol s ref cite journal last1 Ruble first1 J. C. last2 Latham first2 H. A. last3 Fu first3 G. C. year 1997 title Effective Kinetic Resolution of Secondary Alcohols with a Planar Chiral Analogue of 4 dimethylamino pyridine. Use of the Fe C sub 5 sub Ph sub 5 sub Group in Asymmetric Catalysis journal J. Am. Chem. Soc. volume 119 issue 6 pages 1492 1493 url doi 10.1021 ja963835b ref This term is used in chemistry contexts, e.g., for a Chirality chemistry chiral molecule lacking an asymmetric carbon atom, but possessing two non coplanar rings that are each dissymmetric and which cannot easily rotate about the chemical bond connecting them 2,2 dimethylbiphenyl is perhaps the simplest example of this case. Planar chirality is also exhibited by molecules like E cyclooctene , some di or poly substituted metallocene s, and certain monosubstituted paracyclophane s. Nature rarely provides planar chiral molecules, cavicularin being an exception. Assigning the configuration of planar chiral molecules To assign the configuration of a planar chiral molecule, begin by selecting the pilot atom, which is the Cahn Ingold Prelog priority rules highest priority of the atoms that are not in the plane, but are directly attached to an atom in the plane. Next, assign the priority of three adjacent in plane atoms, starting with the atom attached t ... more details
because pyramidalization takes place See pyramidal alkene . cyclooctene trans Cyclooctene is a stable ... center Synthesis of cyclooctene via Cope elimination Alkenes are generated from halo sulfone s in the Ramberg ... more details
The tetrazine ligation is the reaction of a trans cyclooctene and an s tetrazine in an inverse ... strained trans cyclooctene is used as a reactive dienophile . The diene is a 3,6 diaryl ... more details
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