Adamantane-1-thiol

Desulfuration of thiols.7- Aromatic, benzylic, and aliphatic thiols are converted into hydrocarbons when heated in acetic acid with molybdenum carbonyl. The bridgehead adamantane-1-thiol is an exception and gives instead a thioester, RSCOCH3. Yields are 50-90%. The actual reagent is probably tetrakis(acetato)-dimolybdenum.3 Molybdenum carbonyl deposited on silica can also be used. 

Pyridine 1-oxide reacts with adamantane-1-thiol in acetic anhydride to give 2- and 3-(l-adamantanethio)pyridines and their tetrahydropyridine analogues. Corresponding butylthio-substituted pyridines are obtained using Bu SH or Bu SH in this reaction in the presence of a chloroformic acid derivative. No complications arise in the use of 3-bromopyridine 1-oxide and KSH for the synthesis of 3,3 -dipyridyl sulphide. 2-Methyl- or 2-phenyl-pyridine is converted into its 5-alkylthio-homologue by reaction of the pyridine-MeLi adduct with a dialkyl disulphide. ... 

Figure 5.22 Cu UPD on a Au/mica substrate network are filled with adamantane thiol modified by a hybrid nanostructure consisting of (circles), (b) STM images of network-SAM a hydrogen-bonded network and a thiol SAM. hybrid structure with inset showing the (a) Cartoon ofthe hybrid structure and molecular hexagonal thiol island at molecular resolution, structures of the components. The hydrogen- (c, d) Schematic illustrations and STM images of...

PTCDI-melamine network by thiols, (c) STM image of the hybrid structure on Au(lll) with the network filled with adamantane thiol, (d) Illustration of electrochanical Cu deposition in the pores of the network at the thiol/Au interface, (e) STM image of the network after Cu deposition. (Reproduced with permission from Ref. 19. Nature Pubhshing Group, 2008.)... 

Relative reactivity studies of homolytic substitution of monosubstituted benzene derivatives reveal that the 1-adamantyl radical has more pronounced nucleophilic properties than have other, more strained, bridgehead radicals. With benzo-nitrile 21.1) almost exclusive para-substitution is observed, whereas with anisole 0.65) the three possible sites are attacked almost equally. Kinetic studies on the reaction of adamantanethione with adamantane-2-thiol indicate that the rate-controlling chain-propagation step is hydrogen abstraction from the thiol (AdHSH) by the carbon-centred radical AdHSSAd-, and that the main mode of termination involves the diffusion-controlled bimolecular self-reaction of these radicals. ... 

Dao TTH, Guerrouache M, Carbonnier B (2012) Thiol-yne click adamantane monolithic stationary phase fin capillary electrochromatography. Chin J Chem 30 2281-2284... 

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