- Crystal Structure of Burgess Inner Salts and their Hydrolyzed Ammonium Sulfaminates
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The solid-state structures of the Burgess reagent, and its analogous ethyl ester reveal structures indicative of triethylamine solvated sulfonyl imides rather than the more commonly depicted triethylammonium sulfonyl amidate. The existence of a reversibly formed hydrate of Burgess reagent is not supported by present studies, but rather a hydrosylate that does not revert to the Burgess reagent with gentle warming under vacuum was isolated and characterised. Structures of the hydrosylates from both the methyl- and ethyl-amidate esters were determined from X-ray crystallographic analysis and are reported. The crystal structures of the Burgess inner salts exhibit geometries at the sulfur atoms that are intermediate between a planar O2S=NCO2R unit and tetrahedral 4-coordinate sulfur centres that would be expected from a strong single (dative) bond between the triethylamine nitrogen and sulfur. The hydrolysed ammonium sulfaminates are water soluble intermolecular salts composed of triethylammonium ions, Et3NH+, and N-(alkoxycarbonyl)sulfaminate, O(-)SO2NHCO2R {R = CH3 or C2H5}.
- Arduengo, Anthony J.,Uchiyama, Yosuke,DIxon, David A.,Vasiliu, Monica
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p. 867 - 873
(2019/09/03)
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- Burgess Reagent Facilitated Alcohol Oxidations in DMSO
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The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions, and can be combined with other transformations (e.g., Wittig olefinations). A mechanism similar to those described for the Pfitzner-Moffatt and Swern oxidations is proposed.
- Sultane, Prakash R.,Bielawski, Christopher W.
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p. 1046 - 1052
(2018/06/18)
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- A novel, easy and mild preparation of sulfilimines from sulfoxides using the Burgess reagent
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A novel preparation of sulfilimines from the corresponding sulfoxides using the Burgess reagent is described. The reaction is general to dialkyl- and aryl alkyl sulfoxides and proceeds under mild conditions in benzene. A variety of protecting groups can be introduced on the nitrogen of the sulfilimine by choosing the appropriate Burgess reagent.
- Raghavan, Sadagopan,Mustafa, Shaik,Rathore, Kailash
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p. 4256 - 4259
(2008/09/21)
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- A new method for the stereoselective synthesis of α- and β-glycosylamines using the Burgess reagent
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Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts
- Nicolaou,Snyder, Scott A.,Nalbandian, Annie Z.,Longbottom, Deborah A.
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p. 6234 - 6235
(2007/10/03)
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- Stereoselective thermal rearrangement of syn-7-(1,2-Butadienyl)-1-methylbicyclo[2.2.1]hept-2-ene [syn-7-(3-Methylallenyl)-1-methylnorbornene]
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The synthesis and separate thermal rearrangements of (±)-(1R*,4S*,7S*)-7-[(R*)-1,2-butadienyl]-1- methylbicyclo[2.2.1]hept-2-ene (8a) and (±)-(1R*,4S*,7S*)-7-[(S*)-1,2-butadienyl]-1- methylbicyclo[2.2.1]hept-2-ene (8b) are described. Both 8a and 8b are shown to rearrange to (±)-cis-1-ethylidene-3a,4,5,7a-tetrahydro-6-methylindene (9) and (±)-cis-1-ethylindene-3a,4,5,7a-tetrahydro-3a-methylindene (10) with greater than 90% stereoselectivity. Epimer 8a gives predominantly (E)-9 and (Z)-10, whereas 8b gives predominantly (Z)-9 and (E)-10, results consistent with either a six-electron [σ2s + π2s + π2s] Cope or eight-electron [σ2s + π2s + (π2s + π2a)] augmented Cope process. Stereochemical assignments (8a vs 8b, (E)-9 vs (Z)-9, and (E)-10 vs (Z)-10) are based upon experiments in nuclear Overhauser effect (NOE) difference spectroscopy.
- Duncan, James A.,Hendricks, Robert T.,Kwong, Katy S.
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p. 8433 - 8442
(2007/10/02)
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- THERMAL DECOMPOSITION OF ORGANOTIN SULFAMATES: A ONE POT SYNTHESIS OF VINYLTRIBUTYLTIN COMPOUNDS
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The preparation of some alkyltributyltin sulfamates is described.Thermal decomposition of these compounds provides a route to vinyltributyltin derivatives.
- Ratier, Max,Khatmi, Djamel,Duboudin, J.Georges,Minh, Dao The
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p. 285 - 292
(2007/10/02)
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