Abstract
The preparation of adamantanethione from adamantanone is reported, either via 2-ethoxy-2-adamantanethiol or directly with the aid of phosphorus pentasulfide. The conditions for the latter reaction were developed so as to give the highest yield (91%). Dimerization or trimerization of the thioketone under the influence of methanesulfonic acid leads to dispiro[1,3-dithietane-2.2′:4.2″-diadamantane], resp. trispiro[1,3,5-trithiane-2.2′:4.2″:6.2″′-triadamantane]. The spectral properties of the compounds are discussed, especially the n.m.r. spectrum of the thione in connection with the anisotropy of the thiocarbonyl group, and the aromatic solvent-induced shift.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
125 articles.
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