Preparation of 4-Allenyloxazolines from (Z)-2-En-4-yn-1-ol via Propargyl/Allenyl Isomerization
Journal
The Journal of Organic Chemistry
Journal Volume
89
Journal Issue
17
Start Page
12762
End Page
12768
ISSN
0022-3263
1520-6904
Date Issued
2024-08-23
Author(s)
Abstract
A novel method for the preparation of 4-allenyl-oxazolines 2 is described via the reaction of 2-en-4-yn-1-ols 1 with trichloroacetonitrile in the presence of DBU. Reaction proceeds through the nucleophilic attack of OH functionality in 1 to CCl3CN followed by cyclization, propargyl/allene isomerization, and protonation. In this investigation, it is noticed that propargyl/allene isomerization is sensitive to the substituents.
Publisher
American Chemical Society (ACS)
Type
journal article