113314-29-7Relevant articles and documents
ω-HYDROXY-1-ALKANESULFONYL CHLORIDES
King, J. F.,Webster, Michael R.,Chiba, Naoki,Allen, Julie K.,Parker, Kenneth J. M.,et al.
, p. 161 - 176 (2007/10/02)
The general synthesis of hydroxyalkanesulfonyl chlorides is illustrated by the preparation of 6-hydroxy-1-butanesulfonyl cloride (2e) and 5-hydroxy-1-pentanesulfonyl chloride (2d) as fairly stable, only liquids (of ca. 95percent purity) charecterized by Hmr, Cmr and infrared spectra, and by conversion both to the corresponding sultones (3) and to crystalline acetoxy-piperidides (6); 2d and 2e form apparent polymers, very slowly on standing at room temperature and more rapidly on heating, but on reaction with triethylamine yield the sultones (3d and 3e).A sample consisting mostly (>70percent) of 4-hydroxy-1-butanesulfonyl chloride (2c), prepared and charecterized similarly, was found to form the sultone (3c) slowly in non-polar solvents, much more readily in polar media (t1/2 ca. 20 min in water), and very rapidly in the presence of triethylamine.Effective concentrations for the spontaneous cyclization of 4-hydroxy-1-butanesulfonyl chlorides (2c) and the tertiary-amine induced cyclizations of 2d and 2e are estimated at roughly 3x102, 0.1, and 0.05 M, respectively.The mechanism of the chlorination reaction and the origins of the different products with different substrates and reaction conditions are discussed.
