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e oxidative cleavage of olefinic bonds with phi oac 2 nmo and catalytic oso4 organic letters 12 7 1552 5 doi 10 1021 ol100290a pmc 2848477 pmid 20192259 fournier h m 1907 transformation des alcools primaires saturès en acides monobasiques correspondants c r acad sci 331 fournier h m 20 july 1909 sur la préparation des acides gras et de leurs anhydres bull soc chim fr 920 ciufolini m a swaminathan s 1989 synthesis of a model depsipeptide segment of luzopeptins bbm 928 potent antitumor and antiretroviral antibiotics tetrahedron lett 30 23 3027 doi 10 1016 s0040 4039 00 99393 6 chromium based reagents oxidation of alcohols to aldehydes and ketones basic reactions in organic synthesis 2006 pp 1 95 doi 10 1007 0 387 25725 x_1 isbn 0 387 23607 4 song z j zhao m desmond r devine p tschaen d m tillyer r frey l heid r xu f foster b li j reamer r volante r grabowski e j j dolling u h reider p j 1999 practical asymmetric synthesis of an endothelin receptor antagonist j org chem 64 26 9658 doi 10 1021 jo991292t crimmins m t debaillie a c 2006 enantioselective total synthesis of bistramide a j am chem soc 128 15 4936 7 doi 10 1021 ja057686l pmc 2546575 pmid 16608311 nicolaou k c scott tria g edmonds d j 2008 total synthesis of platencin angew chem 120 9 1804 doi 10 1002 ange 200800066 marcos fernández gabriel tojo 2006 oxidation of primary alcohols to carboxylic acids a guide to current common practice basic reactions in organic synthesis berlin springer isbn 0 387 35431 x song z j zhao m desmond r devine p tschaen d m tillyer r frey l heid r xu f foster b li j reamer r volante r grabowski e j j dolling u h reider p j okada s kato y mano e j org chem 1999 64 9658 sharpless k b amberg w bennani y l crispino g a hartung j jeong k s kwong h l morikawa k wang z m xu d zhang x l j org chem 1992 57 2768 bal b s childers jr w e pinnick h w 1981 oxidation of α β unsaturated aldehydes tetrahedron abstract 37 11 2091 doi 10 1016 s0040 4020 01 97963 3 v t e alcohols by consumption alcohols found in alcoholic drinks 1 propanol 2 methyl 1 butanol ethanol isoamyl alcohol isobutanol phenethyl alcohol tert amyl alcohol tert butyl alcohol tryptophol medical alcohol ethchlorvynol methylpentynol methanol poisoning ethanol toxic alcohols isopropyl alcohol methanol primary alcohols 1 methanol 4 methylcyclohexanemethanol aminomethanol cyclohexylmethanol methoxymethanol methylazoxymethanol trifluoromethanol ethanol 1 aminoethanol 2 2 2 trichloroethanol 2 2 2 trifluoroethanol 2 2 ethoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 butoxyethanol 2 chloroethanol 2 ethoxyethanol 2 fluoroethanol 2 mercaptoethanol 2 methoxyethanol aminoethylethanolamine diethylethanolamine dimethylethanolamine ethanol ethanolamine n n diisopropylaminoethanol n methylethanolamine phenoxyethanol tribromoethanol butanol 2 methyl 1 butanol isobutanol n butanol straight chain saturated c 1 c 9 methanol ethanol 1 propanol 1 butanol 1 pentanol 1 hexanol 1 heptanol 1 octanol capryl 1 nonanol pelargonic straight chain saturated c 10 c 19 1 decanol capric 1 undecanol hendecyl 1 dodecanol lauryl 1 tridecanol 1 tetradecanol myristyl 1 pentadecanol 1 hexadecanol cetyl palmityl 1 heptadecanol 1 octadecanol stearyl 1 nonadecanol straight chain saturated c 20 c 29 1 icosanol arachidyl 1 heneicosanol 1 docosanol behenyl 1 tricosanol 1 tetracosanol lignoceryl 1 pentacosanol 1 hexacosanol ceryl 1 heptacosanol 1 octacosanol cluytyl montanyl 1 nonacosanol straight chain saturated c 30 c 39 1 triacontanol melissyl myricyl 1 hentriacontanol 1 dotriacontanol lacceryl 1 tritriacontanol 1 tetratriacontanol geddyl 1 pentatriacontanol 1 hexatriacontanol 1 heptatriacontanol 1 octatriacontanol 1 nonatriacontanol straight chain saturated c 40 c 49 1 tetracontanol 1 hentetracontanol 1 dotetracontanol 1 tritetracontanol 1 tetratetracontanol 1 pentatetracontanol 1 hexatetracontanol 1 heptatetracontanol 1 octatetracontanol 1 nonatetracontanol 2 ethylhexanol allyl alcohol anisyl alcohol benzyl alcohol cinnamyl alcohol crotyl alcohol furfuryl alcohol isoamyl alcohol neopentyl alcohol nicotinyl alcohol perillyl alcohol phenethyl alcohol prenol propargyl alcohol salicyl alcohol tryptophol vanillyl alcohol veratrole alcohol secondary alcohols 2 1 phenylethanol 2 butanol 2 deoxyerythritol 2 heptanol 3 heptanol 2 hexanol 3 hexanol 3 methyl 2 butanol 2 nonanol 2 octanol 2 pentanol 3 pentanol cyclohexanol cyclopentanol cyclopropanol diphenylmethanol isopropanol pinacolyl alcohol pirkle s alcohol propylene glycol methyl ether tertiary alcohols 3 2 methyl 2 pentanol 2 methylheptan 2 ol 2 methylhexan 2 ol 3 methyl 3 pentanol 3 methyloctan 3 ol diacetone alcohol ethchlorvynol methylpentynol nonafluoro tert butyl alcohol tert amyl alcohol tert butyl alcohol triphenylethanol triphenylmethanol hydric alcohols monohydric alcohols methanol c 1 ethanol c 2 isopropanol c 3 1 butanol c 4 1 pentanol c 5 cetyl alcohol c 16 dihydric alcohols ethylene glycol propylene glycol trihydric alcohols glycerol polyhydric alcohols sugar alcohols pentaerythritol ethylene glycol c 2 glycerol propylene glycol c 3 erythritol threitol c 4 xylitol c 5 mannitol sorbitol c 6 volemitol c 7 amyl alcohols 2 2 dimethylpropan 1 ol 2 methylbutan 1 ol 2 methylbutan 2 ol 3 methylbutan 1 ol 3 methylbutan 2 ol pentan 1 ol pentan 2 ol pentan 3 ol aromatic alcohols benzyl alcohol 2 4 dichlorobenzyl alcohol 3 nitrobenzyl alcohol saturated fatty alcohols cetostearyl alcohol decanol lauryl alcohol myristyl alcohol nonanol octanol tridecanol undecanol branched and unsaturated fatty alcohols 3 methyl 3 pentanol erucyl alcohol linolenyl alcohol linoleyl alcohol oleyl alcohol palmitoleyl alcohol tert amyl alcohol tert butyl alcohol sugar alcohols c 1 c 7 methylene glycol c 1 ethylene glycol c 2 glycerol c 3 erythritol c 4 threitol c 4 arabitol c 5 ribitol c 5 xylitol c 5 mannitol c 6 sorbitol c 6 galactitol c 6 iditol c 6 volemitol c 7 deoxy sugar alcohols fucitol cyclic sugar alcohols inositol glycylglycitols maltitol lactitol isomalt maltotriitol maltotetraitol polyglycitol terpene alcohols monoterpene alcohols borneol citronellol geraniol linalool menthol nerol rhodinol terpineol sesquiterpene alcohols bisabolol farnesol nerolidol patchoulol diterpene alcohols phytol dialcohols 1 3 butanediol 1 4 butanediol 1 5 pentanediol 2 methyl 2 propyl 1 3 propanediol diethylpropanediol ethylene glycol trialcohols glycerol sterols cholesterol ergosterol lanosterol β sitosterol stigmasterol fluoroalcohols 1 3 difluoro 2 propanol 2 2 2 trifluoroethanol 2 fluoroethanol nonafluoro tert butyl alcohol trifluoromethanol preparations substitution of haloalkane carbonyl reduction ether cleavage hydrolysis of epoxide hydration of alkene ziegler process reactions deprotonation protonation alcohol oxidation glycol cleavage nucleophilic substitution fischer speier esterification williamson ether synthesis elimination reaction nucleophilic substitution of carbonyl group friedel crafts alkylation nucleophilic conjugate addition transesterification category 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 st...