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Development of a New Benzylating Reagent Spontaneously Releasing Benzyl Cation Equivalents at Room Temperature
Authors:Dr Kohei Yamada  Yuichi Tsukada  Yukiko Karuo  Dr Masanori Kitamura  Prof?Dr Munetaka Kunishima
Institution:Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma‐machi, Kanazawa 920‐1192 (Japan)
Abstract:A new O‐benzylating reagent, that is, 4‐(4,6‐diphenoxy‐1,3,5‐triazin‐2‐yl)‐4‐benzylmorpholinium trifluoromethanesulfonate (DPT‐BM), has been developed. Benzyl cation equivalents are generated from DPT‐BM by dissolving the compound in a solvent at room temperature under non‐acidic conditions. The benzylation of various alcohols by using a combination of DPT‐BM and magnesium oxide provided the benzyl ethers in good yields.
Keywords:alkylation  carbocations  protecting groups  reaction mechanisms  synthetic methods
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