183184-05-6Relevant academic research and scientific papers
Nucleophilic ring opening of cyclic 1,2-sulfites with nitrogen nucleophiles. A route to enantiopure benzylic amino alcohols
Nymann, Kirsten,Mylvaganam, Saravanapavan,Svendsen, John S.
, p. 1060 - 1063 (2007/10/03)
The reaction between cyclic 1,2-sulfites and two imide and two sulfonamide nucleophiles has been investigated in order to develop a procedure for the enantioselective preparation of N-protected vicinal amino alcohols. The results show that both imide and sulfonamide anions react with cyclic sulfites, yielding the desired products. In some cases the regioselectivities are low, and for the sulfonamides products originating from nucleophilic addition to the sulfite sulfur are observed. Acta Chemica Scandinavica 1998.
Nucleophilic reactions between cyclic 1,2-sulfites and chloride ions
Nymann, Kirsten,Jensen, Linda,Svendsen, John S.
, p. 832 - 841 (2007/10/03)
When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio- and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (SN2 reactions) and a retention pathway (SN2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites. Acta Chemica Scandinavica 1996.
