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kauffmann olefination wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 formation of the reagent 2 mechanism 3 applications 4 references toggle the table of contents kauffmann olefination 5 languages deutsch español فارسی தமிழ் 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 type of chemical reaction the kauffmann olefination is a chemical reaction to convert aldehydes and ketones to olefins with a terminal methylene group this reaction was discovered by the german chemist thomas kauffmann and is related to the better known tebbe olefination or wittig reaction formation of the reagent edit the reagent was generated in situ by conversion of different halogenides of molybdenum or tungsten with methyllithium at low temperatures 78 c 1 2 3 4 during the warm up process the formation of the active reagent occurs nmr experiments have shown that the active reagent is not a schrock carbene e g tebbe reagent mechanism edit mechanism experiments shows that the olefination process is a sequence of cycloaddition and cycloelimination steps applications edit for a long time this reaction had no applications in synthetic organic chemistry in 2002 it was used in a total synthesis of the terpene gleenol as a mild and non basic reagent in a one pot protocol with an olefin metathesis step with grubbs catalyst 5 it is remarkable that the organometallic catalyst tolerates the inorganic reaction products references edit t kauffmann m papenberg r wieschollek j sander 1992 organomolybdän und organowolfram reagenzien ii über den carbonylolefinierenden μ methylenkomplex aus mo 2 cl 10 und vier äquivalenten methyllithium chem ber 125 143 148 doi 10 1002 cber 19921250123 t kauffmann p fiegenbaum m papenberg r wieschollek d wingbermühl 1993 organomolybdän und organowolfram reagenzien iii chemoselektive nichtbasische carbonylmethylenierungs reagenzien aus moocl 3 thf 2 und moocl 4 bildung thermolabilität struktur chem ber 126 79 87 doi 10 1002 cber 19931260114 t kauffmann j baune p fiegenbaum u hansmersmann c neiteler m papenberg r wiescholleck 1993 organomolybdän und organowolfram reagenzien iv über die chemoselektivität des carbonylmethylenierenden reagenzes aus 2 moocl 3 thf 2 und 4 ch 3 li chem ber 126 89 96 doi 10 1002 cber 19931260115 t kauffmann 1997 neue reaktionen molybdän und wolframorganischer verbindungen additiv reduktive carbonyldimerisierung spontane umwandlung von methyl in μ methylenliganden und selektive carbonylmethylenierung angew chem 109 12 1312 1329 bibcode 1997angch 109 1312k doi 10 1002 ange 19971091205 k oesterreich i klein d spitzner 2002 one pot reactions total synthesis of the spirocyclic marine sesquiterpene axenol synlett 10 1712 1714 doi 10 1055 s 2002 34211 v t e alkenes alkenes ethene c 2 h 4 propene c 3 h 6 butene c 4 h 8 pentene c 5 h 10 hexene c 6 h 12 heptene c 7 h 14 octene c 8 h 16 nonene c 9 h 18 decene c 10 h 20 polyenes preparations dehydrohalogenation from haloalkane dehydration reaction from alcohol semihydrogenation from alkyne bamford stevens reaction barton kellogg reaction boord olefin synthesis chugaev elimination cope reaction corey winter olefin synthesis grieco elimination hofmann elimination horner wadsworth emmons reaction hydrazone iodination julia olefination kauffmann olefination mcmurry reaction peterson olefination ramberg bäcklund reaction shapiro reaction takai olefination wittig reaction olefin metathesis ene reaction cope rearrangement reactions hydrogenation halogenation hydration electrophilic addition oxymercuration reaction hydroboration cyclopropanation epoxidation dihydroxylation ozonolysis hydrohalogenation polymerization diels alder reaction wacker process dehydrogenation ene reaction friedel crafts alkylation retrieved from https en wikipedia org w index php title kauffmann_olefination oldid 1341116929 categories name reactions carbon carbon bond forming reactions olefination reactions hidden categories articles with short description short description matches wikidata this page was last edited on 1 march 2026 at 14 59 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of 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