Electhophilic allylation of 2,6-dimethylphenol and 2,6-dimethylanisole at meta-positions

✍ Scribed by Bernard Miller; Michael P. McLaughlin

• Book ID: 104246012
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 143 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94987-1

✦ Synopsis

Electrophillc benzylations of 2,6-dimethylphenol and its ethers give surprisingly hia yields of products of attack at m&a-positions of the aromatic rings.1 Examination of possible mechanisms for meta-benzylation showed that only direct attack at the r&a-positions was consistent with sll the evidence. In particular, the possibility that benzylation Initially occurred at ortho-positions was ruled out for reactions of 2,6-dlmethylphenyl ethers, and, by analogy, for reactions of 2,6-dimethylphenol.1

We have now investigated the Frledel-Crafts sllylation of 2,6-dimethylphenol (2,6-DMP) and 2,6--dtithylanisole (2,6-D?@,), and have found that unexpectedly hi& yields of m&a-substitution products are again obtsined. We have demonstrated that initlsl attack at ortho-positions of 2,6-DMP can account for no sore than a small percentage of the yield of meta-sllylatlon product.