Aziridines with benzyne

Wu, Sha, and coworkers found that aziridines react with benzyne to give novel spiroindoles (Scheme 9, equation 1) [34], The products are [4+2] dimers of l-benzyl-2-methyl-eneindolin-3-one. Similar compounds were obtained using Af-substituted aziridines and substituted benzynes. This reaction did not occur with KF or TBAF instead, a-fluoro-p-amino acid derivatives were the products. When water was present, the intermediate aziridinium ion-aryl... 

Fascinating rearrangements of aziridines have been applied to the synthesis of diterpene alkaloids by Wiesner and co-workers (Scheme 40). For example, the ester 217, prepared from cyclopentadiene carboxylate (215) and the benzyne precursor 216 by a Diels-Alder reaction, was converted to the aziridine 218 by treatment with benzenesulfonyl azide in 83% yield. When the aziridine 218 was heated with water for 24 h, the hydroxy ester 219 was obtained in 97% yield subsequent oxidation with the Jones reagent afforded the ketone 220. This rearrangement is analogous to that of the benzenesulfonylaziridine of norbomene. ... 

Benzyne also reacts with oxiranes and aziridines. ... 

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