Burgess reagent

{{Chembox

| ImageFile = Burgess.svg

| ImageSize = 200px

| IUPACName = 1-Methoxy-N-triethylammoniosulfonyl-methanimidate

| OtherNames =

|Section1={{Chembox Identifiers

| InChIKey = YSHOWEKUVWPFNR-UHFFFAOYAN

| CASNo = 29684-56-8

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H5HBH02LFX

| PubChem = 2724994

| ChemSpiderID = 2007108

| EINECS = 629-648-8

| SMILES = O=S(=O)(N=C([O-])OC)[N+](CC)(CC)CC

| InChI = 1/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3

}}

|Section2={{Chembox Properties

| C=8 | H=18 | N=2 | O=4 | S=1

| Appearance =

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| BoilingPt =

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|Section3={{Chembox Hazards

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

| MainHazards =

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The Burgess reagent (methyl N-(triethylammoniumsulfonyl)carbamate) is a mild and selective dehydrating reagent often used in organic chemistry.{{cite journal | title = The reactions of an N-sulfonylamine inner salt |author1=Atkins, G. M. |author2=Burgess, E. M. | journal = J. Am. Chem. Soc. | year = 1968 | volume = 90 | pages = 4744–4745 | doi = 10.1021/ja01019a052 | issue = 17|bibcode=1968JAChS..90.4744A }}{{cite journal | title = Burgess reagent in organic synthesis | author1 = Sachin Khapli, Satyajit Dey | author2 = Dipakranjan Mal | name-list-style = amp | journal = J. Indian Inst. Sci. | year = 2001 | volume = 81 | pages = 461–476 | url = http://journal.library.iisc.ernet.in/vol200104/paper6/sachin.pdf | url-status = dead | archiveurl = https://web.archive.org/web/20040302130947/http://journal.library.iisc.ernet.in/vol200104/paper6/sachin.pdf | archivedate = 2004-03-02 }} It was developed in the laboratory of Edward M. Burgess at Georgia Tech.

The Burgess reagent is used to convert secondary and tertiary alcohols with an adjacent proton into alkenes. Dehydration of primary alcohols does not work well. The reagent is soluble in common organic solvents and alcohol dehydration takes place with syn elimination through an intramolecular elimination reaction. The Burgess reagent is a carbamate and an inner salt. A general mechanism is shown below.

:Image:Burgess mechanism.png