𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Two new examples of the rare C→O migration of ethoxycarbonyl groups

✍ Scribed by Raquel G Soengas; Juan C Estévez; Ramón J Estévez

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
154 KB
Volume
59
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

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-D-allofuranose (8). Similar treatment of ethyl-3-O-benzyl-6-deoxy-6-nitro-D,Lglycero-D-glucoheptofuronate (12) gives 3-O-benzyl-4-O-ethoxycarbonyl-6-deoxy-6-nitro-D-glucopyranose (16).

📜 SIMILAR VOLUMES

ChemInform Abstract: Reversible C⇔N Migr
ChemInform Abstract: Reversible C⇔N Migration of the Ethoxycarbonyl Group in Pyridinium Ylides.
✍ Yu. G. Gololobov; O. V. Dovgan'; I. Yu. Krasnova; P. V. Petrovskii; I. A. Garbuz 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 30 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Reversible C ⇆ N migration of the ethoxy
Reversible C ⇆ N migration of the ethoxycarbonyl group in the reactions of pyridinium and isoquinolinium ylides derived from malonic ester with isocyanates
✍ Yuri G. Gololobov; Olga V. Dovgan; Igor R. Golding; Pavel V. Petrovskii; Irina A 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 221 KB 👁 2 views

## 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