On the synthesis of β-bromohydrine ethers via intermolecular alkoxyl radical addition to bicyclo[2.2.1]heptene

Primary, secondary, and tertiary alkoxyl radicals add exo-selectively to the olefinic pi-bond in bicyclo[2.2.1]heptene to afford exo-2-alkoxybicyclo[2.2.1]kept-3-yl radicals, which are trapped with BrCCl3 preferentially from the endo face to furnish beta-bromohydrine ethers in 23-67% yield. (c) 2007 Elsevier Ltd. All rights reserved.