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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

✍ Scribed by Yuri G. Gololobov; Olga V. Dovgan; Igor R. Golding; Pavel V. Petrovskii; Irina A. Garbuzova

Publisher: John Wiley and Sons
Year: 2002
Tongue: English
Weight: 221 KB
Volume: 13
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.1104

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✦ Synopsis

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). C → N Migration of the COOEt group takes place at room temperature, but, at an elevated temperature, reverse N → C 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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