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Reversible C→N migration of the ethoxycarbonyl group in pyridinium ylides

✍ Scribed by Yu. G. Gololobov; O. V. Dovgan; I. Yu. Krasnova; P. V. Petrovskii; I. A. Garbuzova

Publisher
Springer
Year
2000
Tongue
English
Weight
80 KB
Volume
49
Category
Article
ISSN
1573-9171

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📜 SIMILAR VOLUMES

ChemInform Abstract: Reversible C⇔N Migr
ChemInform Abstract: Reversible C⇔N Migration of the Ethoxycarbonyl Group in Pyridinium Ylides.
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Reversible C ⇆ N migration of the ethoxy
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## 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 roo

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Two new examples of a carbon!oxygen ethoxycarbonyl group shift are described. Treatment of 3-ethoxycarbonylnitromethyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-a-D-allofuranose (4) with Bu 4 NF leads to a rearrangement to 5-O-ethoxycarbonyl-1,2-Oisopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-a