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

35 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

Access to Document

10.1039/b207729a

Link to publication in Scopus

Fingerprint Dive into the research topics of '5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine'. Together they form a unique fingerprint.

Cite this

@article{ce221f7c9613445495a1e66f609e50df,

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.}",

year = "2002",

month = jan,

day = "1",

doi = "10.1039/b207729a",

language = "English",

volume = "20",

pages = "2338--2339",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0036408738&partnerID=8YFLogxK

U2 - 10.1039/b207729a

DO - 10.1039/b207729a

M3 - Article

AN - SCOPUS:0036408738

VL - 20

SP - 2338

EP - 2339

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

ER -