✦ LIBER ✦

Study on the Reaction of Electron-deficient Cyclopropane Derivatives with Arsonium Ylides

✍ Scribed by Ya-Li Chen; Wei-Guo Cao; Wei-Yu Ding; Xiao-Huaa Sun

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 83 KB
Volume: 23
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.200590019

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The reaction of electron‐deficient cyclopropane derivatives, cis‐1‐methoxycarbonyl‐2‐aryl‐6,6‐dimethyl‐5,7‐dioxospiro[2,5]octa‐4,8‐diones with benzoylmethylenetriphenylarsorane (2) and methoxycarbonylmethylene‐triphenylarsorane (4) was found to form cis,trans‐1‐methoxycarbonyl‐2‐aryl‐3‐benzoyl‐7,7‐dimethyl‐6,8‐dioxo‐spiro[3,5]nona‐5,9‐dione (3a–3e) and trans, cis,trans‐5‐[2′‐methoxycarbonyl‐2′‐(triphenylarsoranylidene)acetyl]‐6‐oxo‐3‐aryl‐tetrahydro‐pyran‐2,4‐dicarboxylic acid dimethyl esters (5a–5c) respectively with high stereoselectivity. The possible reaction mechanisms for the formation of the different products were also proposed.

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