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.
Recent Literature
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.
Ring-opening of readily available 2,5-dihydrothiophenes provides access to a
panel of 1,3-dienes which undergo pyrrole formation in the presence of
inexpensive chloramine-T trihydrate. The transformation is conducted in an open
flask and proceeds at ambient temperatures.
F.-L. Haut, N. J. Feichtinger, I. Plangger, L. A. Wein, M. Müller, T.-N. Streit,
K. Wurst, M. Podewitz, T. Magauer, J. Am. Chem. Soc.,
2021, 143, 9002-9008.
A convenient synthesis of 1,5-fused 1,2,4-triazoles in high yields from readily
available N-arylamidines is efficiently promoted by chloramine-T through
direct metal-free oxidative N-N bond formation. The mild nature of the synthesis
and short reaction time are notable advantages of the developed protocol.
A. S. Singh, A. K. Agrahari, S. K. Singh, M. S. Yadav, V. K. Tiwari, Synthesis, 2019, 51,
3443-3450.
