Chloramine-T, N-chloro tosylamide sodium salt
Chloramine-T is a source of electrophilic chlorine. In water, chloramine-T is decomposed to yield hypochlorite, which acts as a disinfectant, and the sulfonamide moiety, which inhibits bacterial grow due to the similarity with para-aminobenzoic acid (a bacterial metabolite). Chloramine-T can therefore be used as a biocide and a mild disinfectant.
Silica gel-DABCO catalyzed oxidation of alcohols to aldehydes with chloramine-T followed by their Morita-Baylis-Hillman reaction with acrylonitrile or methyl acrylate gives good overall yields of the corresponding Morita-Baylis-Hillman adducts. The present work opens up a new and efficient synthetic route to Morita-Baylis-Hillman adducts directly from alcohols in a one-pot operation.
L. D. S. Yadav, V. P. Srivasta, R. Patel, Synlett, 2010, 1047-1050.
Organotrifluoroborates are rapidly and regioselectively converted into organic bromides in excellent yields under mild conditions, using sodium bromide in the presence of chloramine-T.
G. W. Kabalka, A. R. Mereddy, Organometallics, 2004, 23, 4519-4521.
Benzylic hydrocarbons are selectively converted to the corresponding sulfonamides by the [Cu(CH3CN)4]PF6-catalyzed reaction with anhydrous TolSO2NNaCl (chloramine-T). Under the same conditions, representative ethers and olefins are also amidated.
R. Bhuyan, K. M. Nicholas, Org. Lett., 2007, 9, 3957-3959.
A practical, regio- and diastereoselective synthesis of vicinal chloramines from electron-deficient olefins and Chloramine-T is promoted by Brønsted acids in water. This novel protocol is efficient, mild, ecofriendly, and broadly applicable for the aminochlorination of various electron-deficient olefins including α,β-unsaturated ketones, cinnamate, and cinnamide.
X.-L. Wu, G.-W. Wang, J. Org. Chem., 2007, 72, 9398-9401.