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Synthesis of 2,3-Dihydro-1-phenylbenzo[b]phosphole (1-Phenylphosphindane) and Its Use as a Mechanistic Test in the Asymmetric Appel Reaction: Decisive Evidence against Involvement of Pseudorotation in the Stereoselecting Step
Date Issued
2013-09-30
Date Available
2014-09-30T03:00:13Z
Abstract
Racemic 2,3-dihydro-1-phenylbenzo[b]phosphole was obtained by reduction of 1-phenylbenzo[b]phosphole-1-oxide, itself derived by ring-closing metathesis of phenylstyrylvinylphosphine oxide. The title compound was then reoxidized under asymmetric Appel conditions. Comparison of the sense and degree of the stereoselectivity to those obtained with an open-chain analogue indicated that the ring system does not affect the selectivity of the process. This in turn strongly suggests that the stereoselection is not related to pseudorotamer preferences in putative phosphorane intermediates.
Sponsorship
Science Foundation Ireland
Type of Material
Journal Article
Publisher
American Chemical Society
Journal
Journal of Organic Chemistry
Volume
78
Issue
20
Start Page
10500
End Page
10505
Copyright (Published Version)
2013 American Chemical Society
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
File(s)
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Name
CarretalMS_MainTextRevised.pdf
Size
396.66 KB
Format
Adobe PDF
Checksum (MD5)
03d13c61af03a4e91933be6e17469865
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