Journal of the Chemical Society. Perkin transactions I p. 2579 - 2584 (1988)
Update date:2022-07-31
Topics:
Sugimoto, Akira
Yamano, Junzo
Yasueda, Masahiro
Yoneda, Shigeo
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.
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