Tetrahedron

The effects of substituents and solvent polarity oh photochemical [1, 3] sigmatropic shifts. Experimental evidence in favour of the occurrence of sudden

W Peijnenburg, HM Buck

Index: Peijnenburg, W. J. G. M.; Buck, H. M. Tetrahedron, 1988 , vol. 44, # 15 p. 4927 - 4940

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Citation Number: 6

Abstract

Further experimental evidence regarding the occurrence 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 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 ...