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7956082 
Journal Article 
RING-OPENING REACTIONS OF SOME 1-ETHOXYCARBONYLAZIRIDINES WITH ACETIC-ACID IN CYCLOHEXANE 
Takeuchi, H; Koyama, K 
1981 
Yes 
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry
ISSN: 0300-9580 
1 
121-126 
English 
WOS:A1981KZ44200021 
The formation of N-(2-acetoxylalkyl)carbamates by acetolysis of 1-ethoxycarbonylaziridines in cyclohexane follows an A-2 mechanism where the rate is first order in the aziridine and second order in acetic acid. The regiospecificity of the formation and the reactivity can be interpreted by an A-2 mechanism where bond-breaking is more advanced than bond-making, so that these properties are controlled by electronic factors (a so-called borderline A-2 mechanism). However, an A-2 mechanism largely governed by steric hindrance of initial attack and strain relief on opening, respectively, is proposed for cis-aziridines with bulky substituents at 2- and/or 3-positions. N-Allyl-carbamates formed in some cases appear to result from an A-1 mechanism.