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the conditions used to deliver either of the two possible amides 8 two proposed reaction mechanisms for the amide formation from a ketone via schmidt reaction reactions involving alkyl azides edit the scope of this reaction has been extended to reactions of carbonyls with alkyl azides r n 3 this extension was first reported by j h boyer in 1955 9 hence the name boyer reaction for example the reaction of 3 nitrobenzaldehyde with β azido ethanol the boyer reaction variations involving intramolecular schmidt reactions have been known since 1991 5 these are annulation reactions and have some utility in the synthesis of natural products 6 10 such as lactams 11 and alkaloids 12 intramolecular schmidt reaction reactions involving nitromethane ch 3 no 2 edit in 2020 inspired by the nef reaction of nitro compounds the jiao group developed an azide free schmidt reaction with nitromethane as n donor 13 which is recognized as the schmidt jiao reaction 14 with tf 2 o as the activator nitromethane was converted into the highly electrophilic imine species 1 which was then attacked by h 2 o to furnish the hemiacetal intermediate 2 the c n bond subsequently cleaved to generate intermediate 3 followed by elimination of hotf to produce hno in the presence of hco 2 h and acoh reduction of hno afforded the o acetyl hydroxylamine 5 finally reaction of the starting materials with this active n donor delivered the target product through a beckmann type rearrangement subsequently they improved the reaction conditions enabling nitromethane activation through the integration of a homogeneous lewis acid and recyclable heterogeneous brønsted acid 15 schmidt jiao reaction see also edit hofmann rearrangement lossen rearrangement references edit plagens andreas laue thomas m 2005 named organic reactions 2nd ed chichester john wiley sons isbn 0 470 01041 x wolff hans 2011 the schmidt reaction organic reactions 307 336 doi 10 1002 0471264180 or003 08 isbn 978 0471264187 cite journal cs1 maint periodical has isbn link lang s murphy j a 2006 azide rearrangements in electron deficient systems chem soc rev 35 2 146 156 doi 10 1039 b505080d pmid 16444296 schmidt k f 1924 über den imin rest berichte der deutschen chemischen gesellschaft a and b series 57 4 704 723 doi 10 1002 cber 19240570423 1 2 jeffrey aube gregory l milligan 1991 intramolecular schmidt reaction of alkyl azides j am chem soc 113 23 8965 8966 bibcode 1991jachs 113 8965a doi 10 1021 ja00023a065 1 2 nyfeler erich renaud philippe 24 may 2006 intramolecular schmidt reaction applications in natural product synthesis chimia international journal for chemistry 60 5 276 284 doi 10 2533 000942906777674714 koldobskii g i ostrovskii vladimir a gidaspov b v 1978 11 30 schmidt reaction with aldehydes and carboxylic acids russian chemical reviews 47 11 1084 1094 bibcode 1978rucrv 47 1084k doi 10 1070 rc1978v047n11abeh002294 issn 0036 021x s2cid 250898289 crosby ian t shin james k capuano ben 2010 the application of the schmidt reaction and beckmann rearrangement to the synthesis of bicyclic lactams some mechanistic considerations australian journal of chemistry 63 2 211 doi 10 1071 ch09402 issn 0004 9425 j h boyer j hamer 1955 the acid catalyzed reaction of alkyl azides upon carbonyl compounds j am chem soc 77 4 951 954 bibcode 1955jachs 77 951b doi 10 1021 ja01609a045 milligan gregory l mossman craig j aube jeffrey october 1995 intramolecular schmidt reactions of alkyl azides with ketones scope and stereochemical studies journal of the american chemical society 117 42 10449 10459 bibcode 1995jachs 11710449m doi 10 1021 ja00147a006 lei yao jeffrey aubé 2007 cation π control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams communication j am chem soc 129 10 2766 2767 doi 10 1021 ja068919r pmc 2596723 pmid 17302421 wrobleski aaron sahasrabudhe kiran aubé jeffrey may 2004 asymmetric total synthesis of dendrobatid alkaloids preparation of indolizidine 251f and its 3 desmethyl analogue using an intramolecular schmidt reaction strategy journal of the american chemical society 126 17 5475 5481 bibcode 2004jachs 126 5475w doi 10 1021 ja0320018 pmid 15113219 liu jianzhong zhang cheng zhang ziyao wen xiaojin dou xiaodong wei jialiang qiu xu song song jiao ning 2020 01 17 nitromethane as a nitrogen donor in schmidt type formation of amides and nitriles science 367 6475 281 285 doi 10 1126 science aay9501 ding linlin fan yang lu hongjian 2025 skeletal editing based on nitrogen atom manipulation chemical society reviews 54 18 8145 8169 doi 10 1039 d4cs00974f issn 0306 0012 wang weijin liu jianzhong yang licheng song song jiao ning 2024 02 12 a catalytic method to activate nitromethane by the cooperation of homo and heterogeneous catalysis angewandte chemie international edition 63 7 doi 10 1002 anie 202312354 issn 1433 7851 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 ring expansion and contraction ring closing metathesis rupe reaction schmidt reaction semipinacol rearrangement seyferth gilbert homologation sigmatrop...
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