Burgess-type reagent

Aminoalcohols 196 react with Burgess-type reagents 197 to afford unsymmetrical cyclic sulfamides 198 (Equation 42) <2002AGE3866, 2004CEJ5581>. 

Nicolaou et al. <2002AGE3866, 2004CEJ5581> introduced the Burgess-type reagent for the conversion of aromatic aminoalcohols 47 into cyclic sufamides 48 (Equation 8). 

The formation of Burgess-type reagents (75) from chlorosulfonyl isocyanate (CSI) has recently been disclosed. The one-pot synthesis works well with primary, secondary, and tertiary alcohols and amines containing an active hydrogen.21... 

Bolm and collaborators have demonstrated that the sulfoxide to sulfilimine conversion can be performed under solvent-reduced conditions in a ball mill [17]. The reaction of sulfoxide 97 and 2equiv. of Burgess-type reagent 98 produced the corresponding sulfilimine 99 in 68% yield, after a milling for 80 min (Scheme 4.26). For comparison, in solution (THF, reflux, 2h) the same product was obtained in slightly higher yield (78%). 

Synthesis of sulfilimine employing Burgess-type reagent. 

Hendriks CMM, Earners P, Engel J, Bohn C. Sufibxide-to-sulfilimine conversions use of modified Burgess-type reagents. Adv Synth Catal 2013 355 3363-8. 

Dehydration of 124 to the expected 1-seleno-l-vinylcyclopropanes was succesful only with tertiary alcohols of this type it required the use of thionyl chloride in the presence of triethylamine, pyridine or hexamethylphosphorus triamide followed by reaction with potassium t-butoxide in DMSO, or the use of the Burgess reagent... 

Aldoximes are among the most suitable starting materials for the synthesis of nitriles. A plethora of reagents [222-227] has been introduced for this Beckmann-type fragmentation (see Beckmann reaction, under Section 9.3.2.2). Among these are acetic anhydride [223], metal salts [224] or other metal catalysts [225], selenium dioxide [226] and Burgess reagent [227]. In the presence of hahde derivatives [228] or metal salts [229] aldoximes can also be oxidized to nitrile oxides. 

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