110087-09-7Relevant articles and documents
A Photochemical route to 4-Alkyltropones including Nezukone
Cavazza, Marino,Guerriero, Antonio,Pietra, Francesco
, p. 2005 - 2010 (2007/10/02)
An acetonitrile solution of acetylene and 3-methylcyclopent-2-enone (4) was irradiated with Pyrex-filtered light from a mercury lamp to give 5-methylbicyclohept-6-en-2-one (6) and 6-methyl-tricyclo2,7>heptan-3-one (8).These were easily separated and when heated under reflux in ButOH with SeO2 gave the 4-methyltropone valence-tautomer 5-methylbicyclohept-3,6-dien-2-one (10) and 4-methyltropone (12), respectively, the latter in 20percent overall, unoptimized yield.Similar reactions with 3-isopropylcyclopent-2-enone (5) in the place of (4) led to the natural troponoid 4-isoproyltropone (nezukone) (13).