Photochemical generation and absolute reactivity of an allene oxide in solution

Authors
Clay, MD Durber, J Schepp, NP
Citation
Md. Clay et al., Photochemical generation and absolute reactivity of an allene oxide in solution, ORG LETT, 3(24), 2001, pp. 3883-3886
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
24
Year of publication
2001
Pages
3883 - 3886
Database
ISI
SICI code
1523-7060(20011129)3:24<3883:PGAARO>2.0.ZU;2-W
Abstract
[GRAPHICS] A method for the rapid photochemical generation of allene oxides is describ ed that allows absolute rate constants for the reactions of these interesti ng reactive intermediates to be measured. The fluorenylideneallene oxide ge nerated using this method was found to rearrange to the corresponding cyclo propanone with a rate constant of 0.0012 s(-1) in TFE. The lifetime of the allene oxide was significantly reduced in the presence of nucleophiles such as halides, methanol, and water.