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

Article abstract of DOI:10.1055/s-1986-31761

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 withsodium sulfide.