Triphenylphosphine-Induced Ring Contraction of 1,2-Dioxines

Title
Triphenylphosphine-Induced Ring Contraction of 1,2-Dioxines
Publication Date
2004
Author(s)
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Taylor, Dennis K
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
American Chemical Society
Place of publication
United States of America
DOI
10.1021/jo030330c
UNE publication id
une:15754
Abstract
Triphenylphosphine inserts into the peroxide bond of 1,2-dioxines, initiating ring contraction with loss of triphenylphosphine oxide. This process yields dihydrofuran oxides in 54-97% yield from oxirenyl[2,3-c][1,2]dioxines and dihydrofurans from 3,6-dihydro-1,2-dioxines with inversion of stereochemistry at either the 2 or 5 position in the furan product.
Link
link
Citation
The Journal of Organic Chemistry, 69(7), p. 2577-2579
ISSN
1520-6904
0022-3263
Start page
2577
End page
2579

Files:

NameSizeformatDescriptionLink