85267-56-7Relevant academic research and scientific papers
Photochemical Rearrangements of β,γ-Cyclopropyl-β',γ'-epoxy Ketones
Ayral-Kaloustian, Semiramis,Agosta, William C.
, p. 1718 - 1725 (1983)
Ketones 1-5 have been prepared and photolyzed in benzene and in benzene-methanol (λ > 280 nm).Major volatile products were isolated by gas chromatography and their structures determined by a combination of spectroscopic and chemical methods.The products from 1-4 can be explained by way of a α cleavage and selective fission of the carbon-oxygen bond of the epoxide, according to eq 1 (X = O).No effective competition from cleavage of the cyclopropane ring (eq 1, X = CH2) is observed.Reaction of 2 is slow because of steric crowding, and there is evidence for a small amount of competitive photoisomerisation of 2 to 1.In contrast with 1-4, ketone 5 decarbonylates with formation of 5a.
