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- Title
Oxydation von Allylalkoholen mit Blei(IV)-acetat.
- Authors
Ehrenfreund, Josef; Zink, Markus Peter; Wolf, Hans Richard
- Abstract
Lead tetraacetate (LTA) oxidation of the allylic alcohols 1, 10, 14 and 19 leads to the formation of the epoxides 2, 11, 15 and 20, products of a novel internal addition reaction of the electron deficient alcohol oxygen to the allylic double bond. In some cases ( 10, 14) the formation of a new type of acetoxylated enolethers ( 12, 16) is observed. The LTA oxidation of the allylic dienols 21 and 29 gives rise to the formation of the epoxyacetates 25 and 33, products of a similar internal addition reaction. Furthermore, a variety of cyclization products ( 22, 23, 24, 26, 30, 31, 32 and 34) has been isolated whose formation requires an isomerisation of the allylic trans double bond to a cis one.
- Publication
Helvetica Chimica Acta, 1974, Vol 57, Issue 4, p1098
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19740570418