Rearrangement of ethylenic. alpha.-diols (3-butene-1, 2-diols) to ethylenic. alpha.-diols (1-butene-3, 4-diols)

J Gharbi-Benarous, MS Morales-Rios…

Index: Gharbi-Benarous, Josyane; Morales-Rios, Martha S.; Dana, Gilbert Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2039 - 2040

Full Text: HTML

Citation Number: 1

Abstract

When an electron-attracting aromatic group (IC) is used instead of a phenyl group (la), the isomerization is slowed down but the yield is identical (65-70%). In contrast, the tolyl group enhances the dehydration rate of diol (4b) but decreases the yield to about 35%. There is probably, in the first ionization step, more benzylic carbocation leading to the classical dehydration, with migration of the ethylenic gr0up. l