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boekelheide reaction 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 mechanism 2 related reactions 3 references toggle the table of contents boekelheide reaction 4 languages deutsch español فارسی தமிழ் 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 reaction in organic chemistry boekelheide reaction named after virgil carl boekelheide reaction type rearrangement reaction the boekelheide reaction is a rearrangement of α picoline n oxides to hydroxymethyl pyridines it is named after virgil boekelheide who first reported it in 1954 1 originally the reaction was carried out using acetic anhydride which typically required a period at reflux 140 c the reaction can be performed using trifluoroacetic anhydride tfaa which often allows for a room temperature reaction 2 overall reaction of the boekelheide reaction mechanism edit the mechanism of the boekelheide reaction begins by an acyl transfer from the trifluoroacetic anhydride to the n oxide oxygen the α methyl carbon is then deprotonated by the trifluoroacetate anion this sets the molecule up for a 3 3 sigmatropic rearrangement which furnishes the trifluoroacetylated methylpyridine hydrolysis of the trifluoroacetate releases the hydroxymethylpyridine mechanism of the boekelheide reaction related reactions edit 2 chloromethylpyridine can be prepared by treating 2 picoline n oxide with phosphoryl chloride or triphosgene 3 4 wikimedia commons has media related to boekelheide reaction references edit boekelheide v linn w j march 1954 rearrangements of n oxides a novel synthesis of pyridyl carbinols and aldehydes journal of the american chemical society 76 5 1286 1291 bibcode 1954jachs 76 1286b doi 10 1021 ja01634a026 fontenas c bejan e haddou h aït balavoine g g a 23 september 2006 the boekelheide reaction trifluoroacetic anhydride as a convenient acylating agent synthetic communications 25 5 629 633 doi 10 1080 00397919508011399 ash mary lynne pews r garth 1981 the synthesis of 2 chloromethylpyridine from 2 picoline n oxide journal of heterocyclic chemistry 18 5 939 940 doi 10 1002 jhet 5570180518 narendar p gangadasu b ramesh ch china raju b jayathirtha rao v 2004 facile and selective synthesis of chloromethylpyridines and chloropyridines using diphosgene triphosgene synthetic communications 34 6 1097 1103 doi 10 1081 scc 120028642 retrieved from https en wikipedia org w index php title boekelheide_reaction oldid 1297486118 categories chemical reactions organic reactions name reactions hidden categories articles with short description short description is different from wikidata commons category link is on wikidata this page was last edited on 26 june 2025 at 13 50 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 the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents boekelheide reaction 4 languages add topic