✍ Scribed by Grzegorz Mlostoń; Heinz Heimgartner
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The reactions of 3‐phenyl‐1‐azabicyclo[1.1.0]butane (4) with dimethyl dicyanofumarate ((E)‐8) and dimethyl dicyanomaleate ((Z)‐8) lead to the same mixture of cis‐ and trans‐4‐phenyl‐1‐azabicyclo[2.1.1]hexane 2,3‐dicarboxylates (cis‐11 and trans‐11, resp.; Scheme 3). This result of a formal cycloaddition to the central CN bond of 4 is interpreted by a stepwise reaction mechanism via a relatively stable zwitterionic intermediate 10, which could be intercepted by morpholine to give a 1 : 1 : 1 adduct 12, which undergoes a spontaneous elimination of HCN to yield the fumarate 13 (Scheme 4).
📜 SIMILAR VOLUMES
## Abstract Sterically congested 1‐azabicyclo[1.1.0]butanes **1** add hydrazoic acid smoothly at 0–5°, giving 3‐azidoazetidines **2** in good to excellent yields. After hydrogenolysis over Pd/C catalyst, compounds **2** were converted into __N__‐unsubstituted azetidin‐3‐amines **4**. Attempted redu