78698-20-1Relevant academic research and scientific papers
Cycloaddition of Substituted Bicycloocta-2,6-diene with 4-Phenyl-1,2,4-triazoline-3,5-dione
Adam, Waldemar,Lucchi, Ottorino De,Scheutzow, Dieter
, p. 4130 - 4132 (1981)
4,4-Dimethylbicycloocta-2,6-diene (1b) reacts with 4-phenyl-1,2,4-triazoline-3,5-dione to give the rearranged urazole 3b (via dipolar cycloaddition at the more strained C6-C7 double bond) as the only isolable (22percent yield) product, while 3-bromobicycloocta-2,6-diene (1c) affords the ene adduct 7 as the major product (60percent yield) together with a 10percent yield of the rearranged urazole 3c.Both dimethyl substitution at the C4 position and bromo substitution at the C3 position suppress effectively homocycloaddition and dipolar cycloaddition at the less strained C2-C3 double bond.The ene reactivity of the bromo diene 1c is surprising, since neither the parent diene 1a nor the dimethyl diene 1b exhibit this cycloaddition behavior.
