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1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction. / Zaikin, Pavel A.; Dyan, Ok Ton; Fadeev, Dmitry S. et al.

In: Journal of Fluorine Chemistry, Vol. 199, 01.07.2017, p. 20-29.

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

Harvard

Zaikin, PA, Dyan, OT, Fadeev, DS, Gatilov, YV & Borodkin, GI 2017, '1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction', Journal of Fluorine Chemistry, vol. 199, pp. 20-29. https://doi.org/10.1016/j.jfluchem.2017.04.008

APA

Zaikin, P. A., Dyan, O. T., Fadeev, D. S., Gatilov, Y. V., & Borodkin, G. I. (2017). 1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction. Journal of Fluorine Chemistry, 199, 20-29. https://doi.org/10.1016/j.jfluchem.2017.04.008

Vancouver

Zaikin PA, Dyan OT, Fadeev DS, Gatilov YV, Borodkin GI. 1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction. Journal of Fluorine Chemistry. 2017 Jul 1;199:20-29. doi: 10.1016/j.jfluchem.2017.04.008

Author

Zaikin, Pavel A. ; Dyan, Ok Ton ; Fadeev, Dmitry S. et al. / 1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction. In: Journal of Fluorine Chemistry. 2017 ; Vol. 199. pp. 20-29.

BibTeX

@article{12e897fe13bf42eeaecc8f0231cd3f81,
title = "1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction",
abstract = "1,1-Difluoronaphthalene-2(1H)-ones were proposed as novel fluorinated dienophiles for the Diels-Alder reaction. The influence of the diene structure, reaction conditions on the rate and diastereoselectivity of the Diels-Alder cycloaddition was studied. For the reaction of 1,1-difluoronaphthalene-2(1H)-one with cyclopentadiene a good correlation of the logarithm of endo/exo ratio vs solvent polarity parameters were obtained. The role of diene structure and solvent effects were rationalized on the basis of DFT calculations. The factors influencing the reaction energetics were elucidated by distortion-interaction model approach. Cycloaddition-aromatization sequence was developed for the synthesis of annulated naphthalene derivatives.",
keywords = "DFT, Diastereoselectivity, Diels-Alder cycloaddition, Organofluorine compounds, Solvent effects",
author = "Zaikin, {Pavel A.} and Dyan, {Ok Ton} and Fadeev, {Dmitry S.} and Gatilov, {Yurii V.} and Borodkin, {Gennady I.}",
year = "2017",
month = jul,
day = "1",
doi = "10.1016/j.jfluchem.2017.04.008",
language = "English",
volume = "199",
pages = "20--29",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - 1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction

AU - Zaikin, Pavel A.

AU - Dyan, Ok Ton

AU - Fadeev, Dmitry S.

AU - Gatilov, Yurii V.

AU - Borodkin, Gennady I.

PY - 2017/7/1

Y1 - 2017/7/1

N2 - 1,1-Difluoronaphthalene-2(1H)-ones were proposed as novel fluorinated dienophiles for the Diels-Alder reaction. The influence of the diene structure, reaction conditions on the rate and diastereoselectivity of the Diels-Alder cycloaddition was studied. For the reaction of 1,1-difluoronaphthalene-2(1H)-one with cyclopentadiene a good correlation of the logarithm of endo/exo ratio vs solvent polarity parameters were obtained. The role of diene structure and solvent effects were rationalized on the basis of DFT calculations. The factors influencing the reaction energetics were elucidated by distortion-interaction model approach. Cycloaddition-aromatization sequence was developed for the synthesis of annulated naphthalene derivatives.

AB - 1,1-Difluoronaphthalene-2(1H)-ones were proposed as novel fluorinated dienophiles for the Diels-Alder reaction. The influence of the diene structure, reaction conditions on the rate and diastereoselectivity of the Diels-Alder cycloaddition was studied. For the reaction of 1,1-difluoronaphthalene-2(1H)-one with cyclopentadiene a good correlation of the logarithm of endo/exo ratio vs solvent polarity parameters were obtained. The role of diene structure and solvent effects were rationalized on the basis of DFT calculations. The factors influencing the reaction energetics were elucidated by distortion-interaction model approach. Cycloaddition-aromatization sequence was developed for the synthesis of annulated naphthalene derivatives.

KW - DFT

KW - Diastereoselectivity

KW - Diels-Alder cycloaddition

KW - Organofluorine compounds

KW - Solvent effects

UR - http://www.scopus.com/inward/record.url?scp=85018240202&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2017.04.008

DO - 10.1016/j.jfluchem.2017.04.008

M3 - Article

AN - SCOPUS:85018240202

VL - 199

SP - 20

EP - 29

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

ER -

ID: 9976769