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HERON rearrangement of N,N′-diacyl-N,N′-dialkoxyhydrazines — a theoretical and experimental study

✍ Scribed by Stephen A. Glover; Guoning Mo; Arvi Rauk

Book ID
104209073
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
909 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Ab initio calculations at the B3LYP/6-31G* level on N-methoxy-N-dimethylaminoformamide and its rearrangement to methyl formate and 1,l-dimethyldiazene through the HERON reaction, have been carried out in conjunction with an experimental study of the HERON reactions of N,N'-diacyl-N,N'-dialkoxyhydrazines. Substituent effects are in accord with the theoretical properties of the transition state and point to an anomericaily driven process in which donor groups on the anomeric nitrogen and withdrawing groups on the migrating alkoxy oxygen facilitate the rearrangement process.

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