Polymer Supported Magnesium Anthracene: Application in the Synthesis of Benzylic Grignard Reagents
Abstract
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°C to 20°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-benzychloride, 2,4-dimethoxy-5-methyl-1-benzylchloride, 3,5-dimethoxy-4-benzylchloride, 2,4,6-trimethoxy-3-methyl-1-benzylchloride, and 2,5-dimethoxybenzylchloride. Selected allylic halides similarly yield Grignard ...
View more >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°C to 20°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-benzychloride, 2,4-dimethoxy-5-methyl-1-benzylchloride, 3,5-dimethoxy-4-benzylchloride, 2,4,6-trimethoxy-3-methyl-1-benzylchloride, and 2,5-dimethoxybenzylchloride. Selected allylic halides similarly yield Grignard reagents.
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View more >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°C to 20°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-benzychloride, 2,4-dimethoxy-5-methyl-1-benzylchloride, 3,5-dimethoxy-4-benzylchloride, 2,4,6-trimethoxy-3-methyl-1-benzylchloride, and 2,5-dimethoxybenzylchloride. Selected allylic halides similarly yield Grignard reagents.
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Journal Title
Journal of Organometallic Chemistry
Volume
502
Issue
1-2
Subject
Chemical sciences
Inorganic chemistry
Organic chemistry
Other chemical sciences