119521-99-2Relevant articles and documents
Preparation and Chemical Behaviour of exo-Methylene Compounds: Isoelectronic Compounds of 5-Methylenecyclohexa-1,3-diene
Sugimoto, Akira,Yamano, Junzo,Yasueda, Masahiro,Yoneda, Shigeo
, p. 2579 - 2584 (2007/10/02)
Some exo-methylene compounds such as 9-methylene-9,10-dihydrophenanthrene(2) were photolytically prepared and their chemical behaviour was investigated.Treatment of (2) with acid (CF3CO2H) or base (OBut(1-)) led to the formation of 9-methylphenanthrene, with bromine to 9-bromomethylphenanthrene.Reaction with dimethyl acetylenedicarboxylate did not give Diels-Alder adduct but give an ene adduct.Treatment with ethenetetracarbonitrile also gave an ene adduct.Reaction with carbene or carbenoids gave 9,10-dihydrophenanthrene-9-spirocyclopropanes.Reaction with ethenetetracarbonitrile was examined for other exo-methylene compounds, 1-methylene-1,2-dihydronaphtalene and 2-methylene-2,3-dihydrobenzothiophene.The aromatisation may be responsible for the reactions of these exo-methylene compounds except for the reaction with carbenes.
