We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
A New Type of Claisen Rearrangement Involving 1,3-Dipolar Intermediates. Preliminary communication.
- Authors
Malherbe, Roger; Belluš, Daniel
- Abstract
During the reaction of allyl ethers, allyl sulfides and allyl selenides with in situ prepared dichloroketene ( 1), 2 competing pathways are observed. Besides [2+2]-cycloaddition, an unprecedented [3,3]-sigmatropic ( Claisen) rearrangement via a 1,3-dipolar intermediate takes place. It leads to O-, S- or Se-esters of α,α-dichloro-γ, δ-unsaturated acids containing an inverted allylic group. Starting from cyclic n-membered α-vinyl-substituted ethers, lactones with n+4-membered rings are formed. A very facile synthesis of the naturally occurring macrolides (±)-phoracantholide I ( 10) and (±)-phoracantholide J ( 11) illustrates the synthetic utility of this new 'ketene' Claisen rearrangement.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 8, p3096
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610836