Abstract
An efficient and straightforward method has been developed for the preparation of 1-carbamoylcyclopropane-1-carboxylate derivatives via selective hydrolysis of 1-cyanocyclopropane-1-carboxylates by using hydroxylamine and sodium acetate system strategy. The structure of 1-carbamoylcyclopropane-1-carboxylate 2a was further confirmed by X-ray single crystal analysis.
Keywords
References
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