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Syntheses of stable carbonyl ylides by intramolecular carbenic reaction

✍ Scribed by Masashi Hamaguchi; Toshikazu Ibata

Book ID
104243313
Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
108 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

An intermediacy of carbonyl ylides was reported in the thermolysis of epoxides 1 with electron-withdrawing groups, 1,3,4-oxadiazolines, 2 and in the reaction of carbene with carbonyl?

This communication deals with the first finding of synthesis of stable carbonyl ylides (II) having novel type of mesoionic structure (III) by the intramolecular carbene-carbonyl reaction.

The diasocompounds (Ia,b,c) were prepared by the ordinary diaso-transfer reaction 4 of corresponding imides with p-toluenesulfonyl aside in pyridine solution at O°C using triethylamine. 5

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✍ Shigeru Ohta; Bruno Frei; Oskar Jeger 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 593 KB

## Abstract On ^1^n, π\* ‐excitation 5, 6‐epoxy‐2‐hydroxy‐5, 6‐dihydro‐β‐ionone ((__E__)‐4) shows the typical behaviour of a, β‐unsaturated γ, δ‐epoxy ketones undergoing primarily C(γ), O‐cleavage of the oxiran. However, ^1^π, π\*‐excitation of (__E__)−**4** leads to enol ether **10** which is form