5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

Chantal T. Falzon; Ilhyong Ryu; Carl H. Schiesser

doi:10.1039/b207729a

5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

Chantal T. Falzon, Ilhyong Ryu, Carl H. Schiesser

Department of Applied Chemistry

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

36 Scopus citations

Abstract

Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol^-1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.

Original language	English
Pages (from-to)	2338-2339
Number of pages	2
Journal	Chemical Communications
Volume	20
DOIs	https://doi.org/10.1039/b207729a
State	Published - 1 Jan 2002

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title = "5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine",

abstract = "Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol-1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.",

author = "Falzon, {Chantal T.} and Ilhyong Ryu and Schiesser, {Carl H.}",

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T1 - 5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

AU - Falzon, Chantal T.

AU - Ryu, Ilhyong

AU - Schiesser, Carl H.

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol-1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.

AB - Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol-1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.

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DO - 10.1039/b207729a

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JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

ER -

5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

Abstract

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