Cyclopropyl aziridines: Solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Lee J. Silverberg, Javon M. Rabb, Joseph M. Reno, Gang He

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.

Original languageEnglish (US)
Pages (from-to)193-199
Number of pages7
JournalHeterocyclic Communications
Volume20
Issue number4
DOIs
StatePublished - 2014

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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