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

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Title: 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
Authors: Carr, Damien J.
Kudavalli, Jaya S.
Dunne, Katherine S.
Müller-Bunz, Helge
Gilheany, Declan G.
Permanent link: http://hdl.handle.net/10197/5136
Date: 30-Sep-2013
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.
Funding Details: 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
Keywords: OrganometallicOrganometalloidal compounds
DOI: 10.1021/jo401318g
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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