83731-22-0Relevant academic research and scientific papers
Mechanism of Cyclization of Divinyl-N-phenylboranamines
Sobieralski, Ted J.,Hancock, Kenneth G.
, p. 7542 - 7548 (2007/10/02)
High-resolution NMR and mass spectral data were used to deduce the mechanism of nonoxidative photocyclization of divinyl-N-phenylboranamines.Cyclization was found to proceed through an excited singlet state conrotatory electrocyclic ring closure between phenyl and ajacent vinyl groups, followed by an intramolecular suprafacial 1,5-hydrogen shift.Such a mechanism was found to be operating in both the divinylboranamines and the dicycloalkenylboranamines.Irradiation in acetonitrile inhibited vinylic photochemical trans-cis isomerization, yielding predominantly the cycloadduct fron starting material vinyl stereochemistry.
