9. “Dérivés C-glycosyliques: Partie XI. Étude de la chloration d'oximes d'aldéhydo-sucres”
   Tronchet, J. M.; Barbalat-Rey, F.; Le-Hong, N.; Burger, U.
   Carbohydr. Res. 1973, 29, 297-310.

The chlorination of oximes of aldehydo sugars takes place via an S_E2′ mechanism and gives the corresponding gem-chloronitroso derivatives which are in equilibrium with their dimers. The study of the monomer formation from the dimer by n.m.r. spectroscopy at various temperatures indicates a positive difference of standard entropy. The gem-chloronitroso derivatives obtained isomerize into hydroximoyl chlorides.

DOI : 10.1016/S0008-6215(00)83016-5