59592-00-6Relevant articles and documents
Synthesis of 2-amino-2-cyanoadamantane and its derivatives
Popov, Yu. V.,Mokhov, V. M.,Tankabekyan, N. A.,Safronova, O. Yu.
, p. 1387 - 1394,8 (2012/12/12)
Synthetic routes to new amino nitriles with the functional groups at the 2-position of the adamantane core, based on reactions of adamantanonimines with acetone cyanohydrin or of adamantanone cyanohydrin with aliphatic amines, are considered. The products can be used for preparing new biologically active substances, unsymmetrical adamantyl-containing diamines or amino acids.
Sulfur centered 1,3-dipoles. An efficient trapping of adamantanethione-S-sulfide generated in the reaction of adamantanethione with organic azides
Mloston,Romanski,Heimgartner
, p. 437 - 445 (2007/10/03)
The reaction of adamantanethione (1) and an organic azide at 80°C ("two-component reaction") yields the symmetrical 1,2,4-trithiolane 9 and the corresponding adamantylidene imine 10 in nearly equal amounts. Under the same conditions, the "three-component reaction" with 1, phenyl azide and an aromatic thioketone gives the unsymmetrical 1,2,4-trithiolane 12 as the major product, and 9 and imine 13 as by-products. A 1,3-dipolar cycloaddition of an intermediate thiocarbonyl-S-sulfide and a thioketone is proposed as the mechanism for the formation of the trithiolanes. The structure of trithiolane 12a has been established by X-ray crystallography.
