Reactions of 2-(α-Haloalkyl)thiiranes with Nucleophilic Reagents: IV. Alkylation of Sulfonamides with 2-Chloromethylthiirane. Synthesis and Properties of 3-(Arylamino)thietanes

Alkylation of primary and secondary sulfonamides with 2-chloromethylthiirane in the presence of alkali gives the corresponding N-(thiiran-2-ylmethyl)- and/or N-(thietan-3-yl)sulfonamides. The selectivity of the process depends on the solvent: in water, thiirane-thietane rearrangement products are formed exclusively, while ethanol favors Ad-E reaction leading to thiiranylmethyl derivatives. A procedure has been proposed for the synthesis of 3-(arylamino)thietanes which undergo selective acylation at the nitrogen atom. The possibility for synthesizing analogous derivatives of thietane 1-oxide and thietane 1,1-dioxide is considered.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 1046–1057.Original Russian Text Copyright © 2005 by Sokolov, Butkevich, Yuskovets, Tomashevskii, Potekhin.