Domino reactions with 2-fluoro-3-trifluoromethylfurans and -thiophenes [1]

Klaus Burger; Annett Fuchs; Lothar Hennig; Brigitte Helmreich; Dieter Greif

doi:10.1007/s007060170056

Domino reactions with 2-fluoro-3-trifluoromethylfurans and -thiophenes [1]

Klaus Burger
, Annett Fuchs
, Lothar Hennig
, Brigitte Helmreich
, Dieter Greif

University of Leipzig
Biotechnology Group

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

22 Scopus citations

Abstract

The single fluorine atom of 2-fluoro-3-trifluoromethylfurans and -thiophenes can be readily replaced by various nucleophiles. Depending on the substituent pattern, certain products obtained upon nucleophilic substitution with benzyl alcohols are susceptible to [1, 3]- and [1, 5]-benzyl group migrations under very mild conditions. Therefore, these rearrangements can be integrated into domino reactions.

Original language	English
Pages (from-to)	929-945
Number of pages	17
Journal	Monatshefte für Chemie
Volume	132
Issue number	8
DOIs	https://doi.org/10.1007/s007060170056
State	Published - 2001
Externally published	Yes

Keywords

2-Fluoro-3-trifluoromethylfurans
2-Fluoro-3-trifluoromethylthiophenes
3-Trifluoromethyl-2(3H)-furanones
3-Trifluoromethyl-2(3H)-thiophenones
3-Trifluoromethyl-2(5H)-furanones
3-Trifluoromethyl-2(5H)-thiophenones
Domino reactions
[1, 3]- and [1, 5]-benzyl group migrations

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10.1007/s007060170056

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title = "Domino reactions with 2-fluoro-3-trifluoromethylfurans and -thiophenes [1]",

abstract = "The single fluorine atom of 2-fluoro-3-trifluoromethylfurans and -thiophenes can be readily replaced by various nucleophiles. Depending on the substituent pattern, certain products obtained upon nucleophilic substitution with benzyl alcohols are susceptible to [1, 3]- and [1, 5]-benzyl group migrations under very mild conditions. Therefore, these rearrangements can be integrated into domino reactions.",

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T1 - Domino reactions with 2-fluoro-3-trifluoromethylfurans and -thiophenes [1]

AU - Burger, Klaus

AU - Fuchs, Annett

AU - Hennig, Lothar

AU - Helmreich, Brigitte

AU - Greif, Dieter

PY - 2001

Y1 - 2001

N2 - The single fluorine atom of 2-fluoro-3-trifluoromethylfurans and -thiophenes can be readily replaced by various nucleophiles. Depending on the substituent pattern, certain products obtained upon nucleophilic substitution with benzyl alcohols are susceptible to [1, 3]- and [1, 5]-benzyl group migrations under very mild conditions. Therefore, these rearrangements can be integrated into domino reactions.

AB - The single fluorine atom of 2-fluoro-3-trifluoromethylfurans and -thiophenes can be readily replaced by various nucleophiles. Depending on the substituent pattern, certain products obtained upon nucleophilic substitution with benzyl alcohols are susceptible to [1, 3]- and [1, 5]-benzyl group migrations under very mild conditions. Therefore, these rearrangements can be integrated into domino reactions.

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KW - 2-Fluoro-3-trifluoromethylthiophenes

KW - 3-Trifluoromethyl-2(3H)-furanones

KW - 3-Trifluoromethyl-2(3H)-thiophenones

KW - 3-Trifluoromethyl-2(5H)-furanones

KW - 3-Trifluoromethyl-2(5H)-thiophenones

KW - Domino reactions

KW - [1, 3]- and [1, 5]-benzyl group migrations

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VL - 132

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JF - Monatshefte für Chemie

IS - 8

ER -

Domino reactions with 2-fluoro-3-trifluoromethylfurans and -thiophenes [1]

Abstract

Keywords

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