Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines: Dramatic Rate Acceleration with Very High Substrate Tolerance

Teruhiko Ishikawa; Takayuki Kudoh; Juri Yoshida; Ayako Yasuhara; Shinobu Manabe; Seiki Saito

doi:10.1021/ol025906j

Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines: Dramatic Rate Acceleration with Very High Substrate Tolerance

Teruhiko Ishikawa, Takayuki Kudoh, Juri Yoshida, Ayako Yasuhara, Shinobu Manabe, Seiki Saito

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

64 Citations (Scopus)

Abstract

(Matrix Presented) Dicobalt octacarbonyl [Co₂(CO)₈] in acetonitrile at 75 °C triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable at 75 °C in the absence of the cobalt complex.

Original language	English
Pages (from-to)	1907-1910
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	11
DOIs	https://doi.org/10.1021/ol025906j
Publication status	Published - May 30 2002

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Matrix Presented) Dicobalt octacarbonyl [Co2(CO)8] in acetonitrile at 75 °C triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable at 75 °C in the absence of the cobalt complex.",

author = "Teruhiko Ishikawa and Takayuki Kudoh and Juri Yoshida and Ayako Yasuhara and Shinobu Manabe and Seiki Saito",

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T1 - Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines

T2 - Dramatic Rate Acceleration with Very High Substrate Tolerance

AU - Ishikawa, Teruhiko

AU - Kudoh, Takayuki

AU - Yoshida, Juri

AU - Yasuhara, Ayako

AU - Manabe, Shinobu

AU - Saito, Seiki

PY - 2002/5/30

Y1 - 2002/5/30

N2 - (Matrix Presented) Dicobalt octacarbonyl [Co2(CO)8] in acetonitrile at 75 °C triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable at 75 °C in the absence of the cobalt complex.

AB - (Matrix Presented) Dicobalt octacarbonyl [Co2(CO)8] in acetonitrile at 75 °C triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable at 75 °C in the absence of the cobalt complex.

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Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines: Dramatic Rate Acceleration with Very High Substrate Tolerance

Abstract

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