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1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction. / Zaikin, Pavel A.; Dyan, Ok Ton; Fadeev, Dmitry S. и др.
в: Journal of Fluorine Chemistry, Том 199, 01.07.2017, стр. 20-29.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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