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- W3203031644 abstract "Abstract A methylation protocol of adamantane derivatives was investigated and optimized using AlCl 3 and tetramethylsilane as the methylation agent. Substrates underwent exhaustive methylation of all available bridgehead positions with yields ranging from 62 to 86 %, and up to six methyl groups introduced in one step. Scaling‐up of the reaction was demonstrated by performing the >40 gram‐scale synthesis of 1,3,5,7‐tetramethyladamantane with 62 % yield. For several substrates, rearrangements were observed, as well as cleavage of functional groups or C sp 3 −C sp 2 bonds or even cyclohexyl‐adamantyl bonds. Based on mechanistic studies, it is suggested that a reactive methylation complex is formed from tetramethylsilane and AlCl 3 . X‐ray diffraction structures of hexamethylated bis‐adamantyls reveal elongation or widening of sp 3 carbon bonds between adamantyl moieties to 1.585(3) Å and 125.26(9)° due to repulsive H⋅⋅⋅H contacts." @default.
- W3203031644 created "2021-10-11" @default.
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- W3203031644 date "2021-10-01" @default.
- W3203031644 modified "2023-10-07" @default.
- W3203031644 title "Exhaustive One‐Step Bridgehead Methylation of Adamantane Derivatives with Tetramethylsilane" @default.
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- W3203031644 doi "https://doi.org/10.1002/ejoc.202101004" @default.
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