Free radical-mediated addition of peracetylated 1-bromo-β-D-glucopyranosyl chloride to acrylonitrile

Article abstract of DOI:10.1016/S0008-6215(00)90998-4

Dropwise addition of a benzene solution of tri-n-butylstannane to a solution of 2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride in boiling benzene containing acrylonitrile in excess led predominantly, under photolytic conditions, to a mixture of nonononitriles, either chlorinated or unsaturated. Dropwise addition of a benzene solution of tri-n butylstannane to a solution of 2,3,4,6-tetra-O- acetyl-1-bromo-β-D-glucopyranosyl chloride in boiling benzene containing acrylonitrile in excess led predominantly, under photolytic conditions, to a mixture of nonononitriles, either chlorinated or unsaturated.