Sulfonate, potassium amido

The W-process is based on the condensation of potassium amido-sulfonate with formaldehyde, and the nitration of the condensation product as shown in Reaction 7.13 (overleaf). Potassium amidosulfon-ate and formaldehyde are reacted together to produce potassium methyleneamidosulfonate. This product is nitrated to RDX by a mixture of nitric and sulfuric acids. 

An exception exists to the monobasic nature of sulfamic acid when it dissolves ia Hquid ammonia. Sodium, potassium, etc. add both to the amido and sulfonic portions of the molecule to give salts, such as NaSO NHNa. 

This phase-transfer-catalyzed asymmetric Strecker reaction is further elaborated by the use of a-amido sulfone as a precursor of N-arylsulfonyl imine. In this system, the reaction can be conducted with a slight excess of potassium cyanide (1.05 equiv.), and the reaction leads to completion within 2h (Table 5.15) [46b],... 

A Masked Ammonia Equivalent. Weinreb and co-workers described the utility of 3 as an ammonia synthon. TSE-NH2 (3) was reductively alkylated with benzaldehyde in the presence of NaBHj to afford secondary amine 4, which was subsequently 7V-acylated or A-sulfonylated to generate TSE amido compounds such as 5 (eq 2). Removal of the TSE group from 5 was achieved via a /3-elimination using potassium f-butoxide to afford 6 and vinyl sulfone (7), which polymerizes under these conditions. 

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