Trimethylsilyl ethanesulfonamide

Solubility soluble in benzene, chloroform, dichloromethane, ether, methanol and toluene. 

Preparative Methods prepared by reaction of 2-(trimethylsilyl) ethanesulfonyl chloride (accessible from the commercially available sodium salt of the corresponding sulfonic acid or starting from vinyl trimethylsilane) with gaseous ammonia (eq 1).  

Purity recrystallized twice from ether by cooling solutions to -20 °C. 

Handling, Storage, and Precaution shelf-stable solid avoid contact with sources of fluoride ion toxicity unknown. 

Preparation of 7V-Sulfonylimines. The title sulfonamide has been used to generate iV-sulfinyl-2-(trimethylsilyl)ethanesulfo-namide (SES-NSO), which reacts with aldehydes in the presence of BF3 Et20 to form, after loss of SO2, A-sulfonylimine derivatives. These can be trapped with 2,3-dimethylbuta-1,3-diene in Diels-Alder cycloaddition reactions (eq 2) The SES group can then be removed using a fluoride ion source.  

---

Amino sugars. Glycals undergo addition with the iodonium perchlorate and 2-(trimethylsilyl)ethanesulfonamide to afford 2-iodo-l-sulfonamide adducts which are transformed into the protected aminoglycosides on alcoholysis. 

Intramolecular cycloaddition leads to the formation of 2-azabicyclo [4.3.0] nonane 207 (equation 106). When AT-sulfmyl-2-(trimethylsilyl)ethanesulfonamide (208) is used in the imine Diels-Alder reaction, the 2-(trimethylsilyl)ethanesulfonyl group of 210 can be readily removed by cesium fluoride in DMF (equation 107). 

Trimethylsilyl)ethanesulfonamides are usually prepared by reaction of the amine with 2-(trimethylsilyl)ethanesulfonyl chloride in the presence of a suitable base. An improved large scale preparation of this reagent has been published in Organic Syntheses [Scheme 8.142]. In the first step sodium bisulfite is added to trimethylvinylsilane in the presence of the catalytic amount of ten-butyl perbenzoate. The resulting crude sodium sulfonate is then treated with... 

---