19198-33-5Relevant academic research and scientific papers
FLASH VACUUM THERMOLYSIS OF SPIROCYCLOHEXADIENONES
Jenneskens, Leonardus W.,Wolf, Willem H. De,Bickelhaupt, Friedrich
, p. 3779 - 3784 (2007/10/02)
In an attempt to prepare short-bridged hydroxymetacyclophanes 1b-d, the spirocyclohexadienones 2b-d were pyrolyzed by flash vacuum thermolysis (FVT).Instead of 1b-d,variable amounts of 4-(5-hexenyl)phenol (4b) , β-hydroxybenzocycloalkenes (5b-d) and 4-(trans-1-alkenyl)phenols (6c-d) were obtained.The formation of these products is explained by invoking cleavage of a spiro bond in 2 under formation of the intermediate diradical 3 which, depending on the length of the aliphatic chain and on the temperature, has several pathways open for isomerization to spin-paired products.
