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

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

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2017, Volume: 199, Pages: 20-29 Pages count : 10 DOI: 10.1016/j.jfluchem.2017.04.008

Tags

Diels-Alder cycloaddition; Organofluorine compounds; Solvent effects; Diastereoselectivity; DFT

Authors

Zaikin Pavel A. ¹ , Dyan Ok Ton ¹ , Fadeev Dmitry S. ¹ , Gatilov Yurii V. ^1,2 , Borodkin Gennady I. ^1,2

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Acad Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogov St, Novosibirsk 630090, Russia

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.

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

Published print:

Jul 1, 2017

Web of science	WOS:000404204300004
Scopus	2-s2.0-85018240202
Elibrary	31036638
OpenAlex	W2609298361