51113-06-5Relevant academic research and scientific papers
PHOTOCHEMICALLY INDUCED REACTIONS OF CIS,CIS-CYCLOOCTADIENONE
Matlin, Albert R.,Jin, Kyo
, p. 637 - 640 (1989)
Irradiation of 2,7-cyclooctadienone 1 produces cis,trans-2,7-cyclooctadienone 5 which has been characterized by low temperature 13C NMR.Dienone 5 is in equilibrium with a zwitterionic oxyallyl species 6 via B, B' bond formation.Zwitterion 6 forms cycloadducts with ethyl vinyl ether and 2-methoxypropene.
First example of an enone-alkene [2 + 2 + 2] photocycloaddition: 1,3-photocycloaddition of tetramethylethylene across 2,7-cyclooctadienone
Matlin, Albert R.,Lin, Susanne C.,Patel, Hiren R.,Chai, Minghui
, p. 303 - 305 (2008/03/11)
(equation presented) Irradiation of cyclooctadienone (1) in the presence of tetramethylethylene (TME) produces 9,10,10-tetramethyl-11-oxatricyclo[6.3.0.01,7]undec-2-ene (7) in 33% yield. This reaction is the first example of a 1,3-cycloaddition of an alkene across an enone system. This novel cycloaddition suggests that there is substantial interaction between the carbonyl carbon and the β-enone carbon in the triplet excited state of 1.
