Polymer supported magnesium anthracene: application in the synthesis of benzylic Grignard reagents

Article abstract of DOI:10.1016/0022-328X(95)05688-L

Reactions of polystyrene supported magnesium anthracene containing radical anion and dianion sites, 7,7', with benzylic chlorides or bromides, affords Grignard reagents, RMgX, in modest to high yields, in THF at -10 deg C to 20 deg C.Novel benzylic-type Grignard reagents prepared in high yield include those of 2,6-(dichloromethyl)pyridine, 2,6-(dibromomethyl)pyridine, 2,2',2"-trispyridylmethylchloride, 2-methoxy-3-methyl-1-benzylchloride, 2,4-dimethoxy-5-methyl-1-benzylchloride, 3,5-dimethoxy-4-methyl-1-benzylchloride, 2,4,6-trimethoxy-3-methyl-1-benzylchloride, and 2,5-dimethoxybenzylchloride.Selected allylic halides similarly yield Grignard reagents.Keywords: Polymer; Magnesium; Anthracene; Grignard Reagent; Benzylic halide; Styrene