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Reversible C ⇆ N migration of the ethoxycarbonyl group in the reactions of pyridinium and isoquinolinium ylides derived from malonic ester with isocyanates
Authors:Yuri G Gololobov  Olga V Dovgan  Igor R Golding  Pavel V Petrovskii  Irina A Garbuzova
Abstract:Pyridinium and isoquinolinium ylides ( 7 and 12 ) derived from malonic ester react in an unusual manner with isocyanates giving the new pyridinium ylide ( 9 ) and the new isoquinolinium ylide ( 14 ). CN Migration of the COOEt group takes place at room temperature, but, at an elevated temperature, reverse NC migration of the COOEt group proceeds and ylides 9 and 14 are reconverted into the starting ylides 7 and 12 , respectively. © 2002 John Wiley & Sons, Inc. Heteroatom Chem 13:36–45, 2002; DOI 10.1002/hc.1104
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