Sulphonamide radical anions

S) -71, as the important intermediates. The sulphonamide 71 was cleaved to the parent amine 69 with naphthalene radical anion without racemization of the asymmetric centre adjacent to the nitrogen. The deep-green solution of naphthalene anion radical had been prepared by treating a solution of naphthalene in THF with small pieces of sodium under nitrogen. 

Alkyl alkanesulphonates react with Na naphthalene to form first the radical anion, which splits into R + O-SOa R , from which alkanols, alkanes, and alkanesulphinic acids are formed, depending on conditions. Photochemical cleavage of tosylated sterols and terpene alcohols at 254 nm proceeds in moderate yield within 3 h, in ether, to give back the alcohol via RSO2 + RO sulphonamides similarly give amines. ... 

Figure 2 exhibits an example of eel for a sulphonic ester indirectly reduced by a diphenylacetylene anion radical. The occurrence of eel was also15 established experimentally under similar experimental conditions for sulphonyl chlorides (X = C1) and sulphonamides (X = NRXR2). 

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