57969-57-0Relevant academic research and scientific papers
CYCLOPENTENE, 2,5-DIHYDROFURAN, BENZONORBORNADIENE, AND 7-OXABENZONORBORNADIENE IN THE DIENE SYNTHESIS. STEREOCHEMISTRY OF THE REACTIONS AND ORBITAL CONTROL
Plemenkov, V. V.,Katerinich, L. V.
, p. 725 - 730 (2007/10/02)
The diene synthesis reactions of cyclopentene, 2,5-dihydrofuran, benzonorbornadiene, and 7-oxabenzonorbornadiene with phencyclone and 2,5-diphenylisobenzofuran were investigated.It was established that adducts with the endo configuration are formed exclusively in the reactions with phencyclone, adducts with the exoconfiguration are formed preferentially in the reactions with 2,5-diphenylisobenzofuran, and adducts with a syn-oriented methylene (or oxygen) bridge are formed in the case of the bicyclic dienophiles.It was found that the stereochemistry of addition is determined by secondary orbital interactions involving the orbitals of the methylene and oxygen fragments of the dienophiles.
