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The 1,3-Dipolar Cycloadditions of Nitrile Oxides and Nitrile Imines to Alkyl Dicyanoacetates

✍ Scribed by Richard Neidlein; Zhihua Sui

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
561 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The readily available alkyl dicyanoacetates 1 reacted with the 1,3‐dipolar reagents arenecarbonitrile oxides 2′ and arenecarbonitrile imines 5′ to afford 1,2,4‐oxadiazol and 1,2,4‐triazol derivatives. The arenecarbonitrile oxides 2′ with electron‐donating groups on the arene ring gave products 3a–d resulting from addition on both CN groups of 1, and those with electron‐withdrawing groups provided mono‐adducts 4a–e (Scheme 1). Arylnitrile imines 5′ reacted with 1 to offer both bis‐ and mono‐addition products (Scheme 2); the bis‐adducts 8a,b possess an ester structure, whereas the mono‐adducts 6a–d present a ketene‐hemiacetal structure.

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