Dichloro-p-toluenesulfonamide

Cm.OROCARBONSANDCm.OROHYDROCARBONS - RDIG-Cm.ORINATED TOLUENES] (Vol 6) N,N-Dichloro-p-toluenesulfonamide [473-34-7]... 

The A -SES group can be incorporated by treating an aldehyde with (V-sulfinyl-p-trimethylsilylethanesulfonamide (SESNSO) (13), which can be made by treating the sulfonamide (12) with Thionyl Chloride and a catalytic amount of N,N-dichloro-p-toluenesulfonamide (eq 7) (see also N-Sulfinyl-p-toluenesulfonamide). The )V-sulfonyl imine can be used in situ in a number of reactions. For example, the A(-sulfonyl imine from aldehyde (14) reacts with 2,3-dimethylbutadiene (eq 8) to give the Diels-Alder adduct (15). Treatment of (15) with fluoride ion affords the bicyclic lactam (16). Also, the IV-sulfonyl imine derived from isobutyraldehyde and (13) reacts with Vinylmagne-sium Bromide to provide the allylic SES-sulfonamide (17) in 65% yield (eq 9). ... 

Alkylation of 7V-benzyl-p-toluenesulfonamide (12a) with a threefold excess of fra j-l,4-dichloro-2-butene (ila) gives the allylic chloride 11b. which is treated with sodium acetate in DMF followed by hydrolysis to afford the allylic alcohol 10a in an overall 68% yield. 

Nitrile imines can also be prepared conveniently by the oxidation of easily accessible hydrazones (Scheme 5.45). The oxidant generally used is chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide, CAT). Other oxidants such as iodobenzene diacetate (IBD) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone have also been used. 

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