1036278-82-6Relevant articles and documents
Carbenes in polycyclic systems: Generation and fate of potential adamantane-1,3-dicarbenes
Klaic, Lada,Aleskovic, Marija,Veljkovic, Jelena,Mlinaric-Majerski, Kata
, p. 299 - 305 (2008)
Potential formation and reactions of adamantane-1,3-dicarbenes 1-3 generated under different conditions and from different precursors, such as sodium salt of adamantane-1,3-dicarbaldehyde ditosylhydrazone (4a), sodium salt of 1,3-diacetyladamantane ditosylhydrazone (5a), sodium salt of 1,3-dibenzoyladamantane ditosylhydrazone (6a), and 1,3-bis(diazobenzyl) adamantane (7) are reported. Carbene species generated thermally from 4a yielded bishomoa-damantane (15), as a final product, via intramolecular insertion into adjacent C - C bond and formation of putative anti-Bredt olefin species, followed by hydrogen abstraction. Pyrolysis of the same sodium salt 4a in the presence of hydrogen donor n-Bu3SnH afforded 1,3-dimethyladamantane (17). Thermal decomposition of sodium salt 5a afforded 1,3-divinyladamantane (14). However, thermal decomposition of sodium salt 6a and diazo-precursor 7 gave benzonitrile as a sole identified product. On the contrary, photolysis of 7 afforded dimeric azine 21. Finally, the synthetic pathways of novel tosylhydrazone derivatives 4, 5, 6 and their corresponding sodium salts, as well as bis-diazocompound 7 are described. Copyright
