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Purification of Laboratory Chemicals, 8th Edition by W.L.F. Armarego

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Some Organic and Metal-Organic Compounds Used in Nanotechnology

1-Adamantane thiol (tricyclo[3.3.1.13,7]decane-1-thiol) [34301-54-7] C10H16S, M 168.3, m 95-97°, 100-102°, 99-106°, pK ~ 11.2. This thiol was prepared by various methods namely by formation of 1-adamantylisothiourinium bromide from 1-adamanylbromide followed by alkaline hydrolysis [Geigy A.-G. Belg. Pat 629,370 1963, Chem Abstr 60 9167 1963], by refluxing 1-adamantanol with Lawesson’s reagent (see [19172-47-5]) in toluene [Nishio JCS Perkin Trans I 1113 1993, DOI: 10.1039/P19930001113], and by photolysis of N-(1-adamanylcarbonyloxy)pyridin-2-thione [Barton reaction: Barton et al. Tetrahedron Lett 35 6057 1994, DOI: 10.1016/0040-4039(94)88074-3]. The thiol is generally purified by ...

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