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Tetrahedron Letters

Volumn 35, Issue 18, 1994, Pages 2907-2910

Claisen rearrangement of α-(F-alkyl)enol ethers prepared via Wittig olefination of allyl perfluoroalkanoates

(6) Bégué, Jean Pierre a Bonnet Delpon, Danièle a Wu, Shen Weng a M'Bida, Abderrahim a Shintani, Toshiro b Nakai, Takeshi b

a UNIVERSITÉ PARIS SUD (France)

b TOKYO INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0028339138 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)76656-1 Document Type: Article

Times cited : (16)

References (20)

1
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- Welch¹

2
- 0026704748
- The Wittig reaction of perfluoro acid derivatives: access to fluorinated enol ethers, enamines, and ketones
- (1992) The Journal of Organic Chemistry , vol.57 , pp. 3807
- Bégué¹ Bonnet-Delpon² Mesureur³ Née⁴ Wu⁵

3
- 0000513259
- Nouvelle synthese de trifluoromethylcetones et d' /ga-bromo trifluoromethylcetones
- (1988) Journal of Fluorine Chemistry , vol.39 , pp. 271
- Bégué¹ Mesureur²

4
- 0007199054
- Reaktionen mit Phosphinalkylenen, XXVII. Umsetzung von Fluoressigsäureestern mit Phosphinalkylenen. Eine Möglichkeit zur Synthese von Enoläthern α-fluorierter Ketone
- (1970) Chemische Berichte , vol.103 , pp. 2011
- Bestmann¹ Dornaauer² Rostock³

5
- 84989085897
- Determination ofZ andE configurations in trifluoromethylated vinyl compounds:3J(CF) coupling constants as a criterion for configurational assignments
- (1991) Magnetic Resonance in Chemistry , vol.29 , pp. 675
- Bégué¹ Bonnet-Delpon² Mesureur³ Ourévitch⁴

6
- 33847085984
- Titanium-mediated methylene-transfer reactions. Direct conversion of esters into vinyl ethers
- A similar olefination of non-fluorinated esters requires the use of the Tebbe-type alkylidene titanium complexes
- (1980) Journal of the American Chemical Society , vol.102 , pp. 3270
- Pine¹ Zahler² Evans³ Grubbs⁴

7
- 0642376850
- Alkylidenation of ester carbonyl groups by means of a reagent derived from RCHBr2, Zn, TiCl4, and TMEDA. Stereoselective preparation of (Z)-alkenyl ethers
- (1987) The Journal of Organic Chemistry , vol.52 , pp. 4410
- Okazoe¹ Takai² Oshima³ Utimoto⁴

8
- 0000016723
- -Acylation and -allylation of β,β,β-trifluoropropionic esters via the ketene silyl acetals
- (1984) Tetrahedron Letters , vol.25 , pp. 3991
- Yokozawa¹ Nakai² Ishikawa³

9
- 84912945163
- Claisen rearrangements of fluorinated enol ethers: new entries to α-monofluoro and α, α-difluoro carboxylic acids
- (1991) Journal of Fluorine Chemistry , vol.54 , pp. 68
- Nakai¹ Qian² Kobayashi³ Hirasa⁴

10
- 0027196509
- The Synthesis of γ,Δ-Ethylenic Perfluoroalkyl Ketones via Claisen Rearrangement
- 2=H), prepared by an entirely different elimination reaction
- (1993) Synthetic Communications , vol.23 , pp. 1887
- Driss¹ Chaabouni² Baklouti³

11
- 0025963466
- Preparation of trifluoromethyl ketones and related fluorinated ketones
- Review on the chemistry of perfluoroalkyl ketones
- (1991) Tetrahedron , vol.47 , pp. 3207
- Bégué¹ Bonnet-Delpon²

12
- 0003517869
- Energetic and rate effects of the trifluoromethyl group at C-2 and C-4 on the aliphatic Claisen rearrangement
- and references cited therein
- (1990) The Journal of Organic Chemistry , vol.55 , pp. 1813
- Gajewski¹ Gee² Jurayj³

13
- 84912944832
- 3), −75 ppm (s) for 1a ; −84 (t) and −122 ppm (q) for 1b.

14
- 84912911598
- 1H NMR spectral data of these 1,5-dienes are in accord with the assigned structures. The details will be described in a full paper.

15
- 84912920358
- 2=Ph.

16
- 84912947824
- 1H NMR, δ 1.70 (d, 3H), 2.4–2.8 (m, 4H), 4.15 (d, 2H), 5.5–5.9 (m, 3H), 7.0–7.4 (m, 5H).

17
- 84912935742
- 1H NMR, δ 1.10 (d, 3H), 1.9–2.1 (m, 2H), 2.4–2.6 (m, 3H), 2.9–3.1 (m, 1H), 5.10 (d,d, 2H), 5.6–5.8 (m, 1H), 7.0–7.3 (m, 5H).

18
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- The thermal, aliphatic Claisen rearrangement
- Review on the Claisen rearrangement
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- Ziegler¹

19
- 84912924349
- 19F NMR spectroscopy.

20
- 0001458332
- Ketone perfluoro enolates: regioselective and stereoselective synthesis, unique reactivities, and electronic properties
- (1990) Journal of the American Chemical Society , vol.112 , pp. 4602
- Qian¹ Nakai² Dixon³ Smart⁴

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