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Synthesis 1986; 1986(9): 741-743
DOI: 10.1055/s-1986-31761
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The Replacement of the Carbonyl Group of Adamantanone by an Oxygen or Sulfur Atom and the One-step Transformation of 2-Methyladamantan-2-ol into 2-Oxa-adamantane; An Efficient New Synthesis of 2-Oxa- and 2-Thiaadamantane

Hiroshi Suginome* , Shinji Yamada
  • *Organic Synthesis Division, Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Sapporo 060, Japan
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Publication Date:
20 August 2002 (online)

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2-Oxaadamantane is prepared by two methods: From adamantanone by a four-step sequence consisting of Baeyer-Villiger oxidation, reduction or reductive methylation, iodination with ring cleavage, and recyclization, or from 2-methyl-2-adamantanol by a two-step reaction without isolation of intermediates. In a related manner, 2-thiaadamantane is prepared from adamantanone by a five-step sequence consisting of Baeyer-Villiger oxidation, reductive methylation, iodination with ring cleavage, further iodination, and cyclocondensation of 3,7-diiodobicyclo[3.3.1]nonane with sodium sulfide.

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