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

doi:10.1515/hc-2014-0093

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

Penn State Schuylkill

Research output: Contribution to journal › Article › peer-review

3 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 language	English (US)
Pages (from-to)	193-199
Number of pages	7
Journal	Heterocyclic Communications
Volume	20
Issue number	4
DOIs	https://doi.org/10.1515/hc-2014-0093
State	Published - 2014

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1515/hc-2014-0093

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@article{4c24ca2445fc42d686713d0d2d55ca8d,

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

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.",

author = "Silverberg, \{Lee J.\} and Rabb, \{Javon M.\} and Reno, \{Joseph M.\} and Gang He",

note = "Funding Information: Acknowledgments: L.J.S. gratefully thanks Prof. Douglass F. Taber (University of Delaware) for the gift of 1, the late Prof. Charles Russell (Muhlenberg College) for his help with and use of his department{\textquoteright}s instrumentation, Prof. Mark Maroncelli (Penn State University Park) for providing equipment, Prof. Gong Chen (Penn State University Park) for his group{\textquoteright}s assistance with analytical work, Dr. Phillip Smith (Penn State University Park Metabolomics Core Facility, grant NSF MRI 1126373) for HRMS analyses, Prof. Justin DuBois (Stanford University) for his gift of rhodium catalysts, and Penn State Schuylkill for financial support.",

year = "2014",

doi = "10.1515/hc-2014-0093",

language = "English (US)",

volume = "20",

pages = "193--199",

journal = "Heterocyclic Communications",

issn = "0793-0283",

publisher = "Walter de Gruyter GmbH",

number = "4",

}

TY - JOUR

T1 - Cyclopropyl aziridines

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

AU - Silverberg, Lee J.

AU - Rabb, Javon M.

AU - Reno, Joseph M.

AU - He, Gang

N1 - Funding Information: Acknowledgments: L.J.S. gratefully thanks Prof. Douglass F. Taber (University of Delaware) for the gift of 1, the late Prof. Charles Russell (Muhlenberg College) for his help with and use of his department’s instrumentation, Prof. Mark Maroncelli (Penn State University Park) for providing equipment, Prof. Gong Chen (Penn State University Park) for his group’s assistance with analytical work, Dr. Phillip Smith (Penn State University Park Metabolomics Core Facility, grant NSF MRI 1126373) for HRMS analyses, Prof. Justin DuBois (Stanford University) for his gift of rhodium catalysts, and Penn State Schuylkill for financial support.

PY - 2014

Y1 - 2014

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/84943563590

UR - https://www.scopus.com/pages/publications/84943563590#tab=citedBy

U2 - 10.1515/hc-2014-0093

DO - 10.1515/hc-2014-0093

M3 - Article

AN - SCOPUS:84943563590

SN - 0793-0283

VL - 20

SP - 193

EP - 199

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 4

ER -

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

Abstract

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