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sarett oxidation 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 history toggle history subsection 1 1 first appearance 1 2 modifications and improvements 2 preparation of the sarett reagent toggle preparation of the sarett reagent subsection 2 1 techniques 2 2 safety 2 3 collins technique 3 specific applications 4 see also 5 references 6 external links toggle the table of contents sarett oxidation 13 languages العربية čeština deutsch فارسی français italiano 日本語 한국어 nederlands português русский українська 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 organic reaction sarett oxidation named after lewis hastings sarett reaction type organic redox reaction identifiers rsc ontology id rxno 0000547 the sarett oxidation is an organic reaction that oxidizes primary and secondary alcohols to aldehydes and ketones respectively using chromium trioxide and pyridine unlike the similar jones oxidation the sarett oxidation will not further oxidize primary alcohols to their carboxylic acid form neither will it affect carbon carbon double bonds 1 use of the original sarett oxidation has become largely antiquated however in favor of other modified oxidation techniques the unadulterated reaction is still occasionally used in teaching settings and in small scale laboratory research 2 schematic showing the oxidation of generic primary and secondary alcohols into the respective aldehydes and ketones via the sarett oxidation history edit first appearance edit molecular structure of the sarett collins reagent 3 the reaction is named after the american chemist lewis hastings sarett 1917 1999 the first description of its use appears in a 1953 article 4 co authored by sarett that relates to the synthesis of adrenal steroids the paper proposes the use of the pyridine chromium complex cro 3 2c 5 h 5 n to oxidize primary and secondary alcohols the complex would later become known as the sarett reagent modifications and improvements edit although the sarett reagent gives good yields of ketones its conversion of primary alcohols is less efficient furthermore the isolation of products from the reaction solution can be difficult 5 these limitations were partially addressed with the introduction of the collins oxidation 5 the active ingredient in both the sarett reagent is identical to that in the so called collins reagent i e the pyridine complex cro 3 c 5 h 5 n 2 the collins oxidation varies from the sarett oxidation only in that it uses methylene chloride as solvent instead of neat pyridine 5 the initially proposed methods of executing the collins and sarett oxidations were still not ideal however as the sarett reagent s hygroscopic and pyrophoric properties make it difficult to prepare 6 this issues lead to an improvement of the collins oxidation protocol known as the ratcliffe variant 6 7 preparation of the sarett reagent edit techniques edit the brick red color of unreacted chromium trioxide chromic anhydride the sarett reagent was originally prepared in 1953 by addition of chromium trioxide to pyridine 4 the pyridine must be cooled because the reaction is dangerously exothermic slowly the brick red cro 3 transform into the bis pyridine adduct subsequent to the conversion to the sarett reagent it is immediately used 4 safety edit improper handling of chromium trioxide can result in fire the specific methods of the reagent s preparation are critical as improper technique can cause the explosion of the materials 7 some technical improvements to the original methodology have reduced the risks associated with preparation one such recent improvement reduced the likelihood of explosion by using chromic anhydride granules that would immediately sink below the surface of the cooled pyridine upon addition 2 it should also be mentioned that chromium trioxide is a corrosive carcinogen and therefore must be handled with extreme care 8 collins technique edit the original collins oxidation calls for the sarett reagent to be removed from the excess pyridine and dissolved in the less basic methylene chloride 5 7 while the new solvent improves the overall yield of the reaction it also requires the dangerous transfer of the pyrophoric reagent the 1970 ratcliffe variation reduced the risk of explosion by calling for the sarett reagent to be made in situ this was achieved by creating the sarett reagent according to the original protocol using a stirred mixture of pyridine and methylene chloride 6 specific applications edit the sarett oxidation efficiently oxidizes primary alcohols to aldehydes without further oxidizing them to carboxylic acids 7 this key difference from the jones oxidation is that the jones oxidation occurs in the presence of water which adds to the alcohol following oxidation to an aldehyde 7 9 the sarett and collins oxidations occur in the absence of water 7 the sarett oxidation also proceeds under basic conditions which allows for the use of acid sensitive substrates such as those containing certain protecting groups this is dissimilar to other common acidic oxidation reactions such as the baeyer villiger oxidation which would remove or alter such groups additionally the sarett reagent is relatively inert towards double bonds and thioether groups 4 these groups cannot effectively interact with the chromium of the sarett reagent as compared to the chromium in oxidizing complexes used prior to 1953 4 see also edit pyridinium chlorochromate jones oxidation references edit margareta avram 1983 chimie organica p 472 editura academiei republicii socialiste românia 1 2 nagappam arumugam january 2003 a facile synthesis of 2 aroylindoles by the oxidation of 2 arylmethylindoles using sarett reagent synthetic communications 33 12 2313 2320 doi 10 1081 scc 120021513 s2cid 97957064 cameron t stanley clyburne jason ac dubey pramod k grossert j stuart ramaiah k ramanatham j sereda sergei v 2003 compounds of chromium vi the pyridine chromic anhydride complex benzimidazolinium dichromate and three 2 alkyl 1 h benzimidazolinium dichromates canadian journal of chemistry 81 6 612 619 bibcode 2003cajch 81 612c doi 10 1139 v03 042 1 2 3 4 5 poos g i arth g e beyler r e sarett l h 1953 approaches to the total synthesis of adrenal steroids 1v 4b methyl 7 ethylenedioxy 1 2 3 4 4aα 4b 5 6 7 8 10 10a β dodecahydrophenanthrene 4 β ol 1 one and related tricyclic derivatives journal of the american chemical society 75 2 422 bibcode 1953jachs 75 422p doi 10 1021 ja01098a049 1 2 3 4 collins j c w w hess f j frank 1968 dipyridine chromium vi oxide oxidation of alcohols in dichloromethane tetrahedron letters 9 30 3363 3366 bibcode 1968tetl 9 3363c doi 10 1016 s0040 4039 00 89494 0 1 2 3 ratcliffe r rodehorst r 1970 improved procedure for oxidations with the chromium trioxide pyridine complex journal of organic chemistry 35 11 4000 4002 doi 10 1021 jo00836a108 1 2 3 4 5 6 tojo gabriel fernández marcos 2006 oxidation of alcohols to aldehydes and ketones a guide to current common practice new york ny springer isbn 978 0 387 23607 0 chromium trioxide msds j t baker retrieved 2007 09 13 jones oxidation organic chemistry org external links edit sarett oxidation retrieved from https en wikipedia org w index php title sarett_oxidation oldid 1328268960 categories organic oxidation reactions name reactions hidden categories articles with short description short description matches wikidata this page was last edited on 18 december 2025 at 21 37 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 sarett oxidation 13 languages add topic