Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras

Chang Sik Kim, Christian Diez, Keith C. Russell

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Uracil-enediyne chimeras 4, 7, and 8 were prepared and examined for their propensity to undergo Bergman cyclization. Kinetic experiments showed lactam tautomers 7 and 8 reacted up to 25 times faster than lactim ether 4. Determination of the activation energy for each cycloaromatization reaction, along with radical trapping agent dependent studies, indicate the rate differences result from different ground state energies of the starting enediynes.

Original languageEnglish
Pages (from-to)1555-1558
Number of pages4
JournalChemistry - A European Journal
Volume6
Issue number9
StatePublished - May 2 2000

Fingerprint

Enediynes
Uracil
Cyclization
Ground state
Ethers
Activation energy
Lactams
Kinetics
Ether
Experiments

Keywords

  • Cyclizations
  • Diradicals
  • Electrocyclic reactions
  • Enynes
  • Tautomerism

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras. / Kim, Chang Sik; Diez, Christian; Russell, Keith C.

In: Chemistry - A European Journal, Vol. 6, No. 9, 02.05.2000, p. 1555-1558.

Research output: Contribution to journalArticle

Kim, Chang Sik ; Diez, Christian ; Russell, Keith C. / Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras. In: Chemistry - A European Journal. 2000 ; Vol. 6, No. 9. pp. 1555-1558.
@article{c9647113adb94d5ab217c300139d7c4a,
title = "Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras",
abstract = "Uracil-enediyne chimeras 4, 7, and 8 were prepared and examined for their propensity to undergo Bergman cyclization. Kinetic experiments showed lactam tautomers 7 and 8 reacted up to 25 times faster than lactim ether 4. Determination of the activation energy for each cycloaromatization reaction, along with radical trapping agent dependent studies, indicate the rate differences result from different ground state energies of the starting enediynes.",
keywords = "Cyclizations, Diradicals, Electrocyclic reactions, Enynes, Tautomerism",
author = "Kim, {Chang Sik} and Christian Diez and Russell, {Keith C.}",
year = "2000",
month = "5",
day = "2",
language = "English",
volume = "6",
pages = "1555--1558",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "9",

}

TY - JOUR

T1 - Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras

AU - Kim, Chang Sik

AU - Diez, Christian

AU - Russell, Keith C.

PY - 2000/5/2

Y1 - 2000/5/2

N2 - Uracil-enediyne chimeras 4, 7, and 8 were prepared and examined for their propensity to undergo Bergman cyclization. Kinetic experiments showed lactam tautomers 7 and 8 reacted up to 25 times faster than lactim ether 4. Determination of the activation energy for each cycloaromatization reaction, along with radical trapping agent dependent studies, indicate the rate differences result from different ground state energies of the starting enediynes.

AB - Uracil-enediyne chimeras 4, 7, and 8 were prepared and examined for their propensity to undergo Bergman cyclization. Kinetic experiments showed lactam tautomers 7 and 8 reacted up to 25 times faster than lactim ether 4. Determination of the activation energy for each cycloaromatization reaction, along with radical trapping agent dependent studies, indicate the rate differences result from different ground state energies of the starting enediynes.

KW - Cyclizations

KW - Diradicals

KW - Electrocyclic reactions

KW - Enynes

KW - Tautomerism

UR - http://www.scopus.com/inward/record.url?scp=0034595402&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034595402&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0034595402

VL - 6

SP - 1555

EP - 1558

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 9

ER -