The tosyl aziridine 2  of (+)-2-carene 1  has been prepared, and solvolytic reactions of it with weak protic acids studied.  For comparison, the solvolytic reactions of cis-3-carene-tosylazirdine 4  were also studied.  Experimental results combined with Gaussian calculations demonstrate that the cyclopropane and the aziridine in 2  are conjugated, leading to solvolyses that are more rapid than those of the unconjugated aziridine 4 , and opening of both rings in 2 .

Cyclopropyl aziridines: Solvolytic reactions of the tosyl aziridine of (+)-2-carene

245th National Meeting (2013)

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