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

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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 - Jan 1 2014

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Aziridines
Acids
2-carene
3-carene
aziridine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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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.",
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Cyclopropyl aziridines : Solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene. / Silverberg, Lee Jonathan; Rabb, Javon M.; Reno, Joseph M.; He, Gang.

In: Heterocyclic Communications, Vol. 20, No. 4, 01.01.2014, p. 193-199.

Research output: Contribution to journalArticle

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T1 - Cyclopropyl aziridines

T2 - Solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

AU - Silverberg, Lee Jonathan

AU - Rabb, Javon M.

AU - Reno, Joseph M.

AU - He, Gang

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AB - 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.

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