Tetrahedron p. 4927 - 4940 (1988)
Update date:2022-07-29
Topics:
Peijnenburg, W. J. G. M.
Buck, H. M.
Furher experimental evidence regarding the occurence of sudden polarization in acyclic alkenes is presented.It is shown that the yield of formation of the product derived from an intramolecular photochemical <1,3>-OH shift in the 1 is dependent only on the polarity of the solvent employed.This result could be well explained in terms of a stabilization of the zwitterionic intermediate formed upon irradiation of 1 by reorientation polarization of the dipole solvent molecules.Besides this, it was found that replacement of the alkyl group at the terminal carbon atom of the C3-C9 exocyclic double bond in 1 by a phenyl substituent led to the occurence of a photochemical <1.3>-H shift.This directive effect of the substituents at the exocyclic double bond could be well explained on the basis of the sudden polarization model.
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