An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate

Michael F. Mayer; Qinwei Wang; M. Mahmun Hossain

doi:10.1016/S0022-328X(01)00886-5

An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate

Michael F. Mayer, Qinwei Wang, M. Mahmun Hossain

Chemistry and Biochemistry

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

21 Scopus citations

Abstract

The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η⁵-C₅H₅)(CO)₂Fe(THF)] ⁺[BF₄]^-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.

Original language	English
Pages (from-to)	78-83
Number of pages	6
Journal	Journal of Organometallic Chemistry
Volume	630
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(01)00886-5
State	Published - Jul 2 2001

Keywords

Aziridines
Ethyl diazoacetate
Imines
Iron Lewis acid

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10.1016/S0022-328X(01)00886-5

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title = "An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate",

abstract = "The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.",

keywords = "Aziridines, Ethyl diazoacetate, Imines, Iron Lewis acid",

author = "Mayer, {Michael F.} and Qinwei Wang and Hossain, {M. Mahmun}",

note = "Funding Information: We gratefully thank the NIH for partial financial support of this research project. We thank Patrick Barre for the translation of Ref. [16] .",

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T1 - An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate

AU - Mayer, Michael F.

AU - Wang, Qinwei

AU - Hossain, M. Mahmun

N1 - Funding Information: We gratefully thank the NIH for partial financial support of this research project. We thank Patrick Barre for the translation of Ref. [16] .

PY - 2001/7/2

Y1 - 2001/7/2

N2 - The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.

AB - The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.

KW - Aziridines

KW - Ethyl diazoacetate

KW - Imines

KW - Iron Lewis acid

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JF - Journal of Organometallic Chemistry

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An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate

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Keywords

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