112043-40-0Relevant academic research and scientific papers
2,5-cyclohexadien-1-one photochemistry. Reversible type B oxyallyl zwitterion formation from photorearrangements of bicyclo[3.1.0]hex-3-en-2-ones
Schultz, Arthur G.,Reilly, John
, p. 5068 - 5073 (2007/10/02)
Irradiation of 4-cyano-4-[3′-(2-furyl)propyl]-2,5-cyclohexadien-1-one (9a) gave the type B zwitterion-furan cycloadduct 10. Shorter periods of irradiation of 9a enabled isolation of an intermediate, 6-cyano-6-[3′-(2-furyl)propyl]bicyclo[3.1.0)-hex-3-en-2-
Intramolecular Cycloadditions to Oxyallyl Zwitterions Generated from Photorearrangements of 2,5-Cyclohexadien-1-ones
Schultz, Arthur G.,Macielag, Mark,Plummer, Mark
, p. 391 - 395 (2007/10/02)
Photorearrangement of 2,5-cyclohexadien-1-one 9a gave phenols 12 and 13, while 9b gave bicyclohexenone 10b.No evidence for the formation of an azide-zwitterion cycloadduct was obtained from these examples.However, the 3,6-dimethoxy analogue 9c provided the bridged triazene 14, for which X-ray crystallographic studies confirmed structural assignments for 14 and previously obtained triazenes 5a and 5b. 4--3-methoxy-4-(nethoxycarbonyl)cyclohexa-2,5-dien-1-one (17) photorearranged to bicyclohexenone 18 and phenol 19.The 4-acetoxymethyl derivatives 20a and 20b gave the bridged furan adducts 23a, and 23b in excellent yield.Acetoxymethyl-substituted triazene 27 was obtained from 26c; 27 slowly gave alcohol 28 on exposure to the atmosphere.
