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eactions 3 other rearrangement reactions toggle other rearrangement reactions subsection 3 1 1 3 rearrangements 4 see also 5 references toggle the table of contents rearrangement reaction 27 languages العربية català čeština dansk deutsch español euskara فارسی suomi français עברית हिन्दी bahasa indonesia italiano 日本語 한국어 nederlands norsk bokmål português română русский simple english slovenčina svenska українська tiếng việt 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction where a molecule is turned into a structural isomer of itself in organic chemistry a rearrangement reaction is a broad class of organic reactions that involves a change of connectivity usually the term rearrangement refers to intramolecular processes involving modification of carbon skeleton 1 2 3 often a substituent moves from one atom to another atom in the same molecule hence these reactions are usually intramolecular in the example below the substituent r moves from carbon atom 1 to carbon atom 2 1 2 alkyl shift the shifting of an alkyl group in the 1 2 rearragement in a dehydration of an alcohol e1 elimination c r c c c c r c displaystyle underset atop displaystyle color blue ce r ce c ce c c c underset atop displaystyle color blue ce r ce c ce c a rearrangement is not well represented by simple and discrete electron transfers represented by curved arrows in organic chemistry texts the actual mechanism of alkyl groups moving as in wagner meerwein rearrangement probably involves transfer of the moving alkyl group fluidly along a bond not ionic bond breaking and forming in pericyclic reactions explanation by orbital interactions give a better picture than simple discrete electron transfers it is nevertheless possible to draw the curved arrows for a sequence of discrete electron transfers that give the same result as a rearrangement reaction although these are not necessarily realistic in allylic rearrangement the reaction is indeed ionic clarification needed 1 2 rearrangements edit main article 1 2 rearrangement a 1 2 rearrangement is an organic reaction where a substituent moves from one atom to another atom in a chemical compound in a 1 2 shift the movement involves two adjacent atoms but moves over larger distances are possible skeletal isomerization is not normally encountered in the laboratory but is the basis of large applications in oil refineries in general straight chain alkanes are converted to branched isomers by heating in the presence of a catalyst examples include isomerisation of n butane to isobutane and pentane to isopentane highly branched alkanes have favorable combustion characteristics for internal combustion engines 4 further examples are the wagner meerwein rearrangement and the beckmann rearrangement 5 which is relevant to the production of certain nylons 6 pericyclic reactions edit main article pericyclic reactions a pericyclic reaction is a type of reaction with multiple carbon carbon bond making and breaking wherein the transition state of the molecule has a cyclic geometry and the reaction progresses in a concerted fashion examples are hydride shifts and the claisen rearrangement 7 other rearrangement reactions edit 1 3 rearrangements edit 1 3 rearrangements take place over 3 carbon atoms examples the fries rearrangement a 1 3 alkyl shift of verbenone to chrysanthenone see also edit amadori rearrangement curtius rearrangement hofmann rearrangement lossen rearrangement mumm rearrangement photochemical rearrangement pinacol rearrangement schmidt reaction thermal rearrangement of aromatic hydrocarbons tiemann rearrangement wolff rearrangement references edit molecular rearrangement iupac gold book 2014 doi 10 1351 goldbook m03997 march jerry 1985 advanced organic chemistry reactions mechanisms and structure 3rd ed new york wiley isbn 9780471854722 oclc 642506595 rojas christian m ed 2015 molecular rearrangements in organic synthesis doi 10 1002 9781118939901 isbn 978 1 118 34796 6 karl griesbaum arno behr dieter biedenkapp heinz werner voges dorothea garbe christian paetz gerd collin dieter mayer hartmut höke 2002 hydrocarbons ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a13_227 isbn 3 527 30673 0 clayden jonathan greeves nick warren stuart 2012 organic chemistry 2nd ed oxford university press p 958 isbn 978 0 19 927029 3 nuyken oskar pask stephen 25 april 2013 ring opening polymerization an introductory review polymers 5 2 361 403 doi 10 3390 polym5020361 ziegler frederick e december 1988 the thermal aliphatic claisen rearrangement chemical reviews 88 8 1423 1452 doi 10 1021 cr00090a001 v t e topics in organic reactions addition reaction elimination reaction polymerization reagents rearrangement reaction redox reaction regioselectivity stereoselectivity stereospecificity substitution reaction a value alpha effect annulene anomeric effect antiaromaticity aromatic ring current aromaticity baird s rule baker nathan effect baldwin s rules bema hapothle beta silicon effect bicycloaromaticity bredt s rule bürgi dunitz angle catalytic resonance theory charge remote fragmentation charge transfer complex clar s rule conformational isomerism conjugated system conrotatory and disrotatory curtin hammett principle dynamic binding chemistry edwards equation effective molarity electromeric effect electron rich electron withdrawing group electronic effect electrophile evelyn effect flippin lodge angle free energy relationship grunwald winstein equation hammett acidity function hammett equation george s hammond hammond s postulate homoaromaticity hückel s rule hyperconjugation inductive effect kinetic isotope effect lfer solvent coefficients data page marcus theory markovnikov s rule möbius aromaticity möbius hückel concept more o ferrall jencks plot negative hyperconjugation neighbouring group participation 2 norbornyl cation nucleophile kennedy j p orton passive binding phosphaethynolate polar effect polyfluorene ring strain σ aromaticity spherical aromaticity spiroaromaticity steric effects superaromaticity swain lupton equation taft equation thorpe ingold effect vinylogy walsh diagram woodward hoffmann rules woodward s rules y aromaticity yukawa tsuno equation zaitsev s rule σ bishomoaromaticity list of organic reactions carbon carbon bond forming reactions acetoacetic ester synthesis acyloin condensation aldol condensation aldol reaction alkane metathesis alkyne metathesis alkyne trimerisation alkynylation allan robinson reaction arndt eistert reaction auwers synthesis aza baylis hillman reaction barbier reaction barton kellogg reaction baylis hillman reaction benary reaction bergman cyclization biginelli reaction bingel reaction blaise ketone synthesis blaise reaction blanc chloromethylation bodroux chichibabin aldehyde synthesis bouveault aldehyde synthesis bucherer bergs reaction buchner ring expansion cadiot chodkiewicz coupling carbonyl allylation carbonyl olefin metathesis castro stephens coupling chan rearrangement chan lam coupling claisen condensation claisen rearrangement claisen schmidt condensation combes quinoline synthesis corey fuchs reaction corey house synthesis coupling reaction cross coupling reaction cross dehydrogenative coupling cross coupling partner dakin west reaction darzens reaction diels alder reaction doebner reaction wulff dötz reaction ene reaction enyne metathesis ethenolysis favorskii reaction ferrier carbocyclization friedel crafts reaction fujimoto belleau reaction fujiwara moritani reaction fukuyama coupling gabriel colman rearrangement gattermann reaction glaser coupling grignard reaction grignard reagent hammick reaction heck reaction henry reaction heterogeneous metal catalyzed cross coupling high dilution principle hiyama coupling homologation reaction horner wadsworth emmons reaction hydrocyanation hydrovinylation hydroxymethylation ivanov reaction johnson corey chaykovsky reaction julia olefination julia kocienski olefination kauffmann olefination knoevenagel condensation knorr pyrrole synthesis kolbe schmitt reaction kowalski ester homologation kulinkovich reaction kumada coupling liebeskind srogl coupling malonic ester synthesis mannich reaction mcmurry reaction meerwein arylation methylenation michael reaction minisci reaction mizoroki heck vs reductive heck nef isocyanide reaction nef synthesis negishi coupling nierenstein reaction nitro mannich reaction nozaki hiyama kishi reaction olefin conversion technology olefin metathesis palladium nhc complex passerini reaction peterson olefination pfitzinger reaction piancatelli rearrangement pinacol coupling reaction prins reaction quelet reaction ramberg bäcklund reaction rauhut currier reaction reformatsky reaction reimer tiemann reaction rieche formylation ring closing metathesis robinson annulation sakurai reaction seyferth gilbert homologation shapiro reaction sonogashira coupling stetter reaction stille reaction stollé synthesis stork enamine alkylation suzuki reaction takai olefination thermal rearrangement of aromatic hydrocarbons thorpe reaction ugi reaction ullmann reaction wagner jauregg reaction weinreb ketone synthesis wittig reaction wurtz reaction wurtz fittig reaction zincke suhl reaction homologation reactions arndt eistert reaction hooker reaction kiliani fischer synthesis kowalski ester homologation methoxymethylenetriphenylphosphorane seyferth gilbert homologation wittig reaction olefination reactions bamford stevens reaction barton kellogg reaction boord olefin synthesis chugaev elimination cope reaction corey winter olefin synthesis dehydrohalogenation elimination reaction grieco elimination hofmann elimination horner wadsworth emmons reaction hydrazone iodination julia olefination julia kocienski olefination kauffmann olefination mcmurry reaction peterson olefination ramberg bäcklund reaction shapiro reaction takai olefination wittig reaction carbon heteroatom bond forming reactions azo coupling bartoli indole synthesis boudouard reaction cadogan sundberg indole synthesis diazonium compound esterification grignard reagent haloform reaction hegedus indole synthesis hurd mori 1 2 3 thiadiazole synthesis kharasch sosnovsky reaction knorr pyrrole synthesis leimgruber batcho indole synthesis mukaiyama hydration nenitzescu indole synthesis oxymercuration reaction reed reaction schotten baumann reaction ullmann condensation williamson ether synthesis yamaguchi esterification degradation reactions barbier wieland degradation bergmann degradation edman degradation emde degradation gallagher hollander degradation hofmann rearrangement hooker reaction isosaccharinic acid marker degradation ruff degradation strecker degradation von braun amide degradation weerman degradation wohl degradation organic redox reactions acyloin condensation adkins peterson reaction akabori amino acid reaction alcohol oxidation algar flynn oyamada reaction amide reduction andrussow process angeli rimini reaction aromatization autoxidation baeyer villiger oxidation barton mccombie deoxygenation bechamp reduction benkeser reaction bergmann degradation birch reduction bohn schmidt reaction bosch reaction bouveault blanc reduction boyland sims oxidation cannizzaro reaction carbonyl reduction clemmensen reduction collins oxidation corey itsuno reduction corey kim oxidation corey winter olefin synthesis criegee oxidation dakin oxidation davis oxidation deoxygenation dess martin oxidation dna oxidation elbs persulfate oxidation emde degradation eschweiler clarke reaction étard reaction fischer tropsch process fleming tamao oxidation fukuyama reduction ganem oxidation glycol cleavage griesbaum coozonolysis grundmann aldehyde synthesis haloform reaction hydrogenation hydrogenolysis hydroxylation jones oxidation kiliani fischer synthesis kolbe electrolysis kornblum oxidation kornblum delamare rearrangement leuckart reaction ley oxidation lindgren oxidation lipid peroxidation lombardo methylenation luche reduction markó lam deoxygenation mcfadyen stevens reaction meerwein ponndorf verley reduction methionine sulfoxide miyaura borylation mozingo reduction noyori asymmetric hydrogenation omega oxidation oppenauer oxidation oxygen rebound mechanism ozonolysis parikh doering oxidation pinnick oxidation prévost reaction reduction of nitro compounds reductive amination riley oxidation rosenmund reduction rubottom oxidation sabatier reaction sarett oxidation selenoxide elimination shapiro reaction sharpless asymmetric dihydroxylation epoxidation of allylic alcohols sharpless epoxidation sharpless oxyamination stahl oxidation staudinger reaction stephen aldehyde synthesis swern oxidation transfer hydrogenation wacker process wharton reaction whiting reaction wohl aue reaction wolff kishner reduction wolffenstein böters reaction zinin reaction rearrangement reactions 1 2 rearrangement 1 2 wittig rearrangement 2 3 sigmatropic rearrangement 2 3 wittig rearrangement achmatowicz reaction alkyne zipper reaction allen millar trippett rearrangement allylic rearrangement alpha ketol rearrangement amadori rearrangement arndt eistert reaction aza cope rearrangement baker venkataraman rearrangement bamberger rearrangement banert cascade beckmann rearrangement benzilic acid rearrangement bergman cyclization bergmann degradation boekelheide reaction brook rearrangement buchner ring expansion carroll rearrangement chan rearrangement claisen rearrangement cope rearrangement corey fuchs reaction cornforth rearrangement criegee rearrangement curtius rearrangement demjanov rearrangement di π methane rearrangement dimroth rearrangement divinylcyclopropane cycloheptadiene rearrangement dowd beckwith ring expansion reaction electrocyclic reaction ene reaction enyne metathesis favorskii reaction favorskii rearrangement ferrier carbocyclization ferrier rearrangement fischer hepp rearrangement fries rearrangement fritsch buttenberg wiechell rearrangement gabriel colman rearrangement group transfer reaction halogen dance rearrangement hayashi rearrangement hofmann rearrangement hofmann martius rearrangement ireland claisen rearrangement jacobsen rearrangement kornblum delamare rearrangement kowalski ester homologation lobry de bruyn van ekenstein transformation lossen rearrangement mcfadyen stevens reaction mclafferty rearrangement meyer schuster rearrangement mislow evans rearrangement mumm rearrangement myers allene synthesis nazarov cyclization reaction neber rearrangement newman kwart rearrangement overman rearrangement oxy cope rearrangement pericyclic reaction piancatelli rearrangement pinacol rearrangement pummerer rearrangement ramberg bäcklund reaction ri...