Journal of the Chemical Society. Perkin transactions I p. 1493 - 1498 (1996)
Update date:2022-08-24
Topics:
Dang, Hai-Shan
Roberts, Brian P.
4-Methylbenzenesulfonyl azide reacts with allyltriphenylstannane (ATPS) in refluxing benzene, in the presence of 2,2′-azobis(2-methylpropionitrile) as initiator, to give N-allyl-4-methylbenzenesulfonamide in good yield after hydrolytic work-up. Small amounts of allyl 4-methylphenyl sulfone were also formed. The reaction follows a free-radical chain mechanism which involves competitive addition of Ph5Sn? to Na and to Nc of the azido group in ArSO2NaNbNc. Addition to Na followed by loss of nitrogen gives ArSO2NSnPh3, the precursor of the N-allylarenesulfonamide, while addition to Nc leads to the formation of ArSO2 and thence to the allyl aryl sulfone. Allyltrimethylstannane behaves in a similar way to ATPS, but allyltributylstannane gives only a low yield of N-allylarenesulfonamide and the major product is the unsubstituted sulfonamide MeC6H4SO2NH2, which results because the radical ArSO2NSnBu3 undergoes intramolecular 1,5-hydrogen-atom transfer in preference to adding to the allylstannane. 2-Methylallyltriphenylstannane reacts in an analogous way to ATPS, but allylstannanes containing non-terminal double bonds do not react successfully. The arenesulfonyl azides 4-XC6H4SO2N3 (X = H, MeO, F) react in a similar way to tosyl azide, but the reaction is very sluggish when X = NO2? With 1-octanesulfonyl azide, reaction with Ph3Sn? is much less selective and products arising from attack at Na and Nc are formed in comparable yields. Ethyl azidoformate reacts with allylstannanes in a similar manner to, although more slowly than, tosyl azide and gives good yields of the corresponding allylic carbamates.
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