Journal of the American Chemical Society p. 7542 - 7548 (1982)
Update date:2022-08-02
Topics:
Sobieralski, Ted J.
Hancock, Kenneth G.
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.
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