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Highly Selective Synthesis of [(Z)-3-Chloro-2-(phenylselanyl)-1-alkenyl]phosphonates and 2-Ethoxy-4-(phenylselanyl)-2,5-dihydro-1,2-oxaphosphole 2-Oxides by Electrophilic Reaction of 1,2-Alkadienylphosphonates with PhSeCl

✍ Scribed by Guangke He; Yihua Yu; Chunling Fu; Shengming Ma

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
295 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The reactions of monosubstituted 1,2‐alkadienylphosphonates with PhSeCl in THF or dioxane/H~2~O (10:1) at 70 °C afforded the selenochlorination products [(Z)‐3‐chloro‐2‐(phenylselanyl)‐1‐alkenyl]phosphonates with very high chemo‐ and stereoselectivity, whereas the same reaction with di‐ and trisubstituted allenylphosphonates afforded 2‐ethoxy‐4‐(phenylselanyl)‐2,5‐dihydro‐1,2‐oxaphosphole 2‐oxides exclusively. It was interesting to note that the stereoselctivity for the selenochlorination reaction is opposite to that of the iodo‐ and selenohydroxylation reactions of (allenyl)diphenylphosphane oxides with Cl^–^ acting as the nucleophile. The stereoselectivity of the cyclization reaction is clearly different from that of the selenochlorination reaction.

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