Oxidative addition/cycloaddition of arenesulfonamides and triflamide to N-allyltriflamide and N,N-diallyltriflamide

Abstract

N-Allyltriflamide adds triflamide in the oxidative system (t-BuOCl + NaI) to give N,N′,N′′-propane-1,2,3-triyltris(triflamide), while under the same conditions arenesulfonamides as well as trifluoroacetamide diastereoselectively give the product of chlorination/dimerization, (2R,5S)-2,5-bis(chloromethyl)-1,4-bis[(trifluoromethyl)sulfonyl]piperazine. N,N-Diallyltriflamide reacted with triflamide affords the products of iodotriflamidation of one or two CC bonds, and the product of intramolecular iodotriflamidation, 3,7-diiodo-1,5-bis[(trifluoromethyl)sulfonyl]-1,5-diazocane, and 3,7,9-tris[(trifluoromethyl)sulfonyl]-3,7,9-triazabicyclo[3.3.1]nonane. In contrast, with arenesulfonamides and trifluoroacetamide, N,N-diallyltriflamide gives the products of iodoamidation or/and iodochlorination at only one double bond.