NBS-promoted reactions of symmetrically hindered methylphenols via p-benzoquinone methide

W Baik, HJ Lee, JM Jang, S Koo…

文献索引：Baik, Woonphil; Lee, Hyun Joo; Jang, Jung Min; Koo, Sangho; Kim, Byeong Hyo Journal of Organic Chemistry, 2000 , vol. 65, # 1 p. 108 - 115

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被引用次数: 35

摘要

Symmetrically hindered methylphenols 1 react smoothly with NBS to form transient intermediates, p-benzoquinone methides (BM), which can be further processed to give hydroxybenzaldehydes in the presence of DMSO. This reaction is initiated by the formation of the phenoxy radical, followed by disproportionation to afford BM. None of the side-chain- brominated product is observed. The existence of BM is supported by the following ...