Synthese d'une serie de N-alkyl et N-aroxysulfonylcarbamates de 1-F-alkyl-2-thiophenylethyle

Article abstract of DOI:10.1080/10426500701566980

The action of 1-F-alkyl-2-thiophenylethanols on substituted isocyanates gives the corresponding 1-F-alkyl-2-thiophenylethyl-N-alkyl and N-aroxysulfonylcarbamates in good yields. The reaction was performed in dichloromethane under nitrogen atmosphere at ro

Full text of DOI:10.1080/10426500701566980

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Synthese D'une Serie
de N-Alkyl et N-
Aroxysulfonylcarbamates de 1-
F-Alkyl-2-Thiophenylethyle
I. Chehidi a , H. Zoghlami a & A. Baklouti a
a Laboratoire de Chimie Structurale Organique,
Faculté des Sciences de Tunis , Campus
Universitaire , Tunis, Tunisie
Published online: 20 Feb 2008.
To cite this article: I. Chehidi , H. Zoghlami & A. Baklouti (2007) Synthese D'une
Serie de N-Alkyl et N-Aroxysulfonylcarbamates de 1-F-Alkyl-2-Thiophenylethyle,
Phosphorus, Sulfur, and Silicon and the Related Elements, 183:1, 183-193, DOI:
10.1080/10426500701566980
To link to this article: http://dx.doi.org/10.1080/10426500701566980
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Phosphorus, Sulfur, and Silicon, 183:183–193, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701566980
Synthese D’une Serie de N-Alkyl et
N-Aroxysulfonylcarbamates de
1-F-Alkyl-2-Thiophenylethyle
I. Chehidi, H. Zoghlami, and A. Baklouti
Laboratoire de Chimie Structurale Organique, Faculte´ des Sciences de
Tunis, Campus Universitaire, Tunis, Tunisie
The action of 1-F-alkyl-2-thiophenylethanols on substituted isocyanates gives
the corresponding 1-F-alkyl-2-thiophenylethyl-N-alkyl and N-aroxysulfonyl-
carbamates in good yields. The reaction was performed in dichloromethane under
nitrogen atmosphere at room temperature.
Keywords Carbamates; F-alkylthiophenylethanols; isocyanates
INTRODUCTION
La re´action d’addition des compose´s hydroxyle´s sur les isocyanates con-
duit aux carbamates correspondants dont les proprie´te´s pesticides,1
herbicides,2 anti-cance´reuses,3−6 et anti-sida7 ont e´te´ bien e´tablies. De
nombreux travaux re´alise´s dans notre laboratoire ont e´te´ consacre´s a`
l’e´tude de la re´activite´ des isocyanates d’aroxy et d’alcoxy sulfonyle vis-
a`-vis de divers nucle´ophiles comme les thiols,8 les alcools F-alkyle´s,9
les diols F-alkyle´s,10 les amines hautement fluore´es,11 les aminoalcools
polyfluore´s12ainsi que le 1-F-octyl-2-fluoroe´thanol.13 Dans le meˆme or-
dre d’ide´es, nous avons fait re´agir des 1-F-alkyl-2-thiophe´nyle´thanols
sur une se´rie d’isocyanates diversement substitue´s ce qui nous a per-
mis de synthe´tiser une se´rie de carbamates posse´dant les groupements
F-alkyle et thiophe´nyle.
RESULTATS ET DISCUSSION
Les nucle´ophiles s’additionnent sur les isocyanates et conduisent aux
produits d’addition nucle´ophile correspondants. Dans le cas des alcools
Received January 6, 2007; accepted July 6, 2007.
Address correspondence to I. Chehidi, Laboratoire de Chimie Structurale Organique,
Faculte´ des Sciences de Tunis, Campus Universitaire, El MANAR, 2092 Tunis, Tunisie.
E-mail: ikram.chehidi@gnet.tn
183

184
I. Chehidi et al.
l’addition nucle´ophile sur les isocyanates donne des carbamates selon
la re´action:
´
SCHEMA 1
Lorsque l’alcool est tertiaire et encombre´ comme l’adamantan-1-ol14
ou le tertiobutanol15 et en pre´sence d’isocyanates N-sulfonyle´s, les car-
bamates obtenus subissent une de´carboxylation et se transforment en
sulfamates.
Pour les 1-F-alkyl-2-thiophe´nyle´thanols, la re´action d’addition
nucle´ophile fournit les carbamates correspondants selon le me´canisme
re´actionnel suivant:
´
SCHEMA 2
Le sche´ma 2 ci-dessous re´sume les re´sultats obtenus:
Vis-a`-vis du chlorosulfonylisocyanate, le comportement de ces 1-F-
alkyl-2-thiophe´nyle´thanols est diffe´rent de celui des autres alcools sim-
ples ou F-alkyle´s. Avec les alcools simples la re´action se traduit apre`s
chauffage, par la formation des alcoxysulfonylisocyanates correspon-
dants dont l’obtention est due d’apre`s les donne´es de la litte´rature a` la
se´rie d’e´quilibres suivants:

Sulfonylcarbamates de 1-F-Alkyl-2-Thiophenylethyle
185
´
SCHEMA 3
´
SCHEMA 4
Etant donne´ que les chlorosulfonylcarbamates ont e´te´ isole´s a` basse
tempe´rature, nous pensons qu’a` haute tempe´rature il y a transforma-
tion de ces produits d’addition conforme´ment au me´canisme ci-dessous
plutoˆt que retour a` l’e´quilibre initial.
´
SCHEMA 5

186
I. Chehidi et al.
Cette transformation qui de´bute par une SNi n’a pas lieu avec les
1-F-alkyl-2-thiophe´nyl-e´thanols a` cause probablement du phe´nome`ne
d’encombrement ste´rique des groupements F-alkyle et thiophe´nyle. Par
contre le caracte`re tre`s hygroscopique du chlorosulfonylcarbamate en-
traˆıne, en pre´sence d’humidite´, la formation du carbamate correspon-
dant, suite a` l’hydrolyse du groupement chlorosulfonyle, conforme´ment
au sche´ma:
´
SCHEMA 6
Le Tableau I regroupe l’ensemble des carbamates que nous avons
synthe´tise´s.
Avec les aroxysulfonylisocyanates les rendements sont e´leve´s et les
temps de re´action courts compare´s a` ceux des isocyanates simples. Cela
pourrait eˆtre explique´ par la pre´sence du groupement sulfonyle qui
augmente le caracte`re e´lectrophile du carbone de l’isocyanate.14
PARTIE EXPERIMENTALE
Les spectres RMN ont e´te´ re´alise´s sur un appareil Brucker AC300 a`
300 MHz pour 1H, 75 MHz pour 13C et 282 MHz pour 19F. L’attribution
des signaux des groupements difluoro-me´thyle`nes des chaˆınes RF est
effectue´e selon: CF3-CF2(7)-CF2(6)-CF2(5)-CF2(4)-CF2(3)-CF2(2)-CF2(1). Les
spectres IR ont e´te´ enregistre´s sur un appareil Perkin Elmer Paragon
1000PC.
Les phe´nylisocyanates, n-butylisocyanate, cyclohexylisocyanate, et
chlorosulfonylisocyanate sont des produits commerciaux. Les arox-
ysulfonylisocyanates ont e´te´ pre´pare´s par action des phe´nols cor-
respondants sur l’isocyanate de chlorosulfonyle.16,17 Les 1-F-alkyl-
2-thiophe´nyle´thanols sont obtenus par re´action d’ouverture des
e´poxypropanes F-alkyle´s par le thiophe´nol en pre´sence de triton B.18

187

188
I. Chehidi et al.
Synthe`se des N-alkyl et N-aroxysulfonylcarbamates de
1-N-alkyl-2-thiophe´nyle´thyle
A 10 mmol d’isocyanate dissous dans 10 mL de dichlorome´thane anhy-
dre, on ajoute 10 mmol de 1-F-alkyl-2-thiophe´nyle´thanol dissous dans
10 mL du meˆme solvant. Le milieu re´actionnel est maintenu sous agi-
tation a` la tempe´rature ambiante et sous atmosphe`re d’azote, pendant
trois heures pour les alkylisocyanates et trente min pour les aroxysul-
fonylisocyanates. On e´vapore ensuite le solvant sous vide et on se´pare
les produits par chromatographie sur colonne de gel de silice en utilisant
comme e´luant le me´lange (e´ther die´thylique/e´ther de pe´trole: 30/70). On
recristallise enfin les produits dans le cyclohexane.
N-Phe´nylcarbamate de 1-Tride´cafluorooctyl-
2-thiophe´nyle´thyle (2a)
P.F.: 91–92◦C; IR (CHCl3), υ (cm−1): 3369 (NH); 1771 (C O); 1300–
1
1100 (CF); RMN H (CDCl3, TMS): δ = 3.19 (syst AB, J = 14.0 Hz,
AB
3 J = 10.2 Hz, 3 J = 4.5 Hz, 2H, SCH2 ); 5.55 (m, 1H, CH O);
AX
BX
6.46 (s, 1H, NH); 7.17 (m, 10Harom); RMN 13C{ H} (CDCl3, TMS): δ
1
= 33.7 (s, C3); 69.2 (m, C2); 114–137 (m, Carom), 153.0 (s, C1); RMN
19F (CDCl3, CFCl3): δ = −81.1 (t, 3F, CF3); −120.7 (m, 2F, CF2(1),
J
FF
=
289.0 Hz); −121.9 (m, 2F, CF2(2)); −123.6 (m, 2F, CF2(3)); −124.9 (m, 2F,
CF2(4)); −126.1 (m, 2F, CF2(5)); HRMS: M+ calcule´e 591.0537, trouve´e
591.0559.
N-Phe´nylcarbamate de 1-Heptade´cafluorooctyl-
2-thiophe´nyle´thyle (2b)
P. F.: 102–103◦C; IR (CHCl3), υ(cm−1): 3351 (NH); 1778 (C O); 1300–
1
1100 (CF); RMN H (CDCl3, TMS): δ = 3.21 (syst AB, J = 14.0 Hz,
AB
3 J = 10.2 Hz, 3 J = 4.4 Hz, 2H, SCH2 ); 5.58 (m, 1H, CH O );
AX
BX
6.47 (s, 1H, NH); 7.21 (m, 10Harom); RMN 13C (CDCl3, TMS): δ = 33.7

Sulfonylcarbamates de 1-F-Alkyl-2-Thiophenylethyle
189
(s, C3); 69.3 (m, C2); 115.0–137.2 (m, Carom); 151.1 (s, C1); RMN 19F
(CDCl3,CFCl3): δ = −81.6 (t, 3F, CF3), −119.2 (m, 2F, CF2(1), JFF = 285.0
Hz); −122.2 (m, 2F, CF2(2)); −122.6 (m, 6F, CF2(3−5)); −123.5 (m, 2F,
CF2(6)), −127.6 (m, 2F, CF2(7)). HRMS: M+ calcule´e 691.0473, trouve´e
691.0450.
N-Cyclohexylcarbamate de 1-Tride´cafluorooctyl-2-
thiophe´nyle´thyle (2c)
P. F.: 97–98◦C; IR (CHCl3), υ(cm−1): 3374 (NH); 1760 (C O); 1300–
1100 (CF); RMN 1H (CDCl3, TMS): δ 1.05–1.83 (m, 10H, (CH2)5); 3.12
3
(syst AB, J = 14.0 Hz, J = 10.5 Hz,3 J = 4.9 Hz, 2H, SCH2 );
AB
AX
BX
3.4 (m, 1H, N CH ); 4.62 (d, 3 J = 8.0 Hz, 1H, NH); 5.48 (m, 1H,
HH
CH O); 7.26 (m, 5Harom); RMN 13C (CDCl3, TMS): δ = 24.5 (s, C1);
25.6 (s, C2); 29.9 (s, C3); 33.4 (s, C7); 50.5 (s, C4); 68.5 (m, C6); 127.2 (s,
C11); 128.9 (s, C10); 131.8 (s, C9); 134.8 (s, C8); 153.6 (s, C5); RMN 19F
(CDCl3,CFCl3): δ = −81.7 (t, 3F, CF3); −120.7 (m, 2F, CF2(1), JFF = 284.0
Hz); −122.0 (m, 2F, CF2(2)); −123.6 (m, 2F, CF2(3)); −124.9 (m, 2F,CF2(4));
−126.8 (m, 2F, CF2(5)). HRMS: M+ calcule´e 597.1007, trouve´e 597.1029.
N-Cyclohexylcarbamate de 1-Heptade´cafluorooctyl-
2-thiophe´nyle´thyle (2d)
P. F.: 106–107◦C; IR (CHCl3), υ(cm−1): 3374 (NH); 1762 (C O); 1300–
1
1100 (CF); RMN H (CDCl3, TMS)): δ = 1.00–1.82 (m, 10H, (CH2)5);
3.12 (syst AB, J = 14.0 Hz, 3 J = 10.5 Hz,3 J = 4.8 Hz, 2H,
AB
AX
SCH2 ); 3.37 (m, 1H, N CH ); 4.59 (d, J = B8X.0 Hz, 1H, NH);
3
HH
5.47 (m, 1H, CH O); 7.23 (m, 5Harom); RMN 13C (CDCl3,TMS): δ =
24.5 (s, C1); 25.3 (s, C2); 29.6 (s, C3); 33.4 (s, C7); 50.2 (s, C4); 68.5
(m, C6); 127.3 (s, C11); 129.0 (s, C10); 131.2 (s, C9); 134.4 (s, C8); 153.0
(s, C5); RMN 19F (CDCl3,CFCl3): δ = −82.0 (t, 3F, CF3); −121.7 (m,

190
I. Chehidi et al.
2F, CF2(1), J = 286.0 Hz); −122.8 (m, 8F, CF2(2−5)); −123.7 (m, 2F,
FF
CF2(6)); −127.1 (m, 2F, CF2(7)). HRMS: M+ calcule´e 697.0943 , trouve´e
697.0967.
N-n-Butylcarbamate de 1-Tride´cafluorooctyl-2-
thiophe´nyle´thyle (2e)
P. F.: 95–96◦C; IR (CHCl3), υ (cm−1): 3365 (NH); 1763 (C O); 1300–
1100 (CF); RMN 1H (CDCl3, TMS): δ = 0.85 (t, 3 J
= 7.0 Hz,
HH
3H, CH3); 1.20 (m, 2H, CH2); 1.32 (m, 2H, CH2); 3.17 (m, 4H,
NCH2 et SCH2 ); 4.65 (s, 1H, NH); 5.53 (m, 1H, CH O);
7.20 (m, 5H); RMN 13C (CDCl3, TMS): δ = 13.5 (s, C1); 20.2 (s, C2);
31.2 (s, C3); 33.0 (s, C7); 39.6 (s, C4); 69.4 (m, C6); 128.0 (s, C11);
130.1 (s, C10); 132.5 (s, C9); 135.1 (s, C8); 157.0 (s, C5); RMN 19F
(CDCl3,CFCl3): δ = −81,4 (t, 3F, CF3); −119.7 (m, J = 285.0 Hz, 2F,
FF
CF2(1)); −122.8 (m, 2F, CF2(2)); −123.6 (m, 2F, CF2(3)); −124.3 (m, 2F,
CF2(4)); −126.2 (m, 2F, CF2(5)); HRMS: M+ calcule´e 571.0850, trouve´e
571.0879.
N-n-Butylcarbamate de 1-Heptade´cafluorooctyl-2-
thiophe´nyle´thyle (2f)
P. F.: 100–101◦C; IR (CHCl3), υ(cm−1): 3370 (NH); 1771 (C O); 1300–
3
1100 (CF); RMN 1H (CDCl3, TMS): δ = 0.85 (t, JHH = 7.0 Hz, 3H,
CH3); 1.23 (m, 2H, CH2); 1.34 (m, 2H, CH2); 3.25 (m, 2H, NCH2 et
SCH2 ); 4,65 (s, 1H, NH); 5.60 (m, 1H, CH O); 7.25 (m, 5H); RMN
13C (CDCl3, TMS): δ = 13.6 (s, C1); 20.0 (s, C2); 31.0 (s, C3); 33.5 (s, C7);
41.4 (s, C4); 68.8 (m, C6); 127.4 (s, C11); 129.1 (s, C10); 131.5 (s, C9); 133.7
(s, C8); 154.0 (s, C5); RMN 19F (CDCl3,CFCl3): δ = −81.7 (t, 3F, CF3);
−118.7 (m, J = 286.0 Hz, 2F, CF2(1)); −122.5 (m, 8F, CF2(2−5)); −123.6
FF
(m, 2F, CF2(6)); −127.0 (m, 2F, CF2(7)). HRMS: M+ calcule´e 671.0786,
trouve´e 647.0797.

Sulfonylcarbamates de 1-F-Alkyl-2-Thiophenylethyle
191
N-(2,4,6)-Trime´thylphe´noxysulfonylcarbamate de
1-Tride´cafluorooctyl-2-thiophe´nyl-e´thyle (2g)
P. F.: 80–81◦C; IR (CHCl3), υ(cm−1): 3374 (NH); 1763 (C O); 1384
1
et 1171 (SO2); 1300–1100 (CF); RMN H (CDCl3, TMS): δ = 2.20 (s,
3H, CH3); 2.35 (s, 6H, CH3); 3.23 (syst AB, J = 13.9 Hz, 3 J = 10.5
AB
AX
Hz,3 J = 4.8Hz, 2H, SCH2 ); 5.54 (m, 1H, CH O); 6.94 (s, 1H,
BX
NH); 7.43 (m, 7Harom); RMN 13C (CDCl3,TMS): δ = 16.9 (s, C1); 20.6
(s, C2); 33.5 (s, C5); 71.1 (m, C4); 127.7-137.2 (m, Carom); 148.6 (s, C3);
RMN 19F (CDCl3,CFCl3): δ = −81,6 (t, 3F, CF3); -120.4 (m, J = 286.0
FF
Hz, 2F, CF2(1)); −123.1 (m, 2F, CF2(2)); −123.6 (m, 2F, CF2(3)); −124.5
(m, 2F, CF2(4)); −126.1 (m, 2F, CF2(5)). HRMS: M+ calcule´e 713.0575,
trouve´e 713.0596.
N-(2,4,6)-Trime´thylphe´noxysulfonylcarbamate de
1-Heptade´cafluorooctyl-2-thiophe´nyl-e´thyle (2h)
P. F.: 89–90◦C; IR (CHCl3), υ(cm−1): 3362 (NH); 1779 (C O); 1376 et
1141 ( SO2); 1300–1100 (CF); RMN 1H: (CDCl3, TMS): δ = 2.22 (s, 3H,
3
CH3); 2.35 (s, 6H, CH3); 3.28 (syst AB, J = 13.8 Hz, J = 10.5 Hz,
AB
AX
3 J = 4.6 Hz, 2H, SCH2 ); 5.53 (m, 1H, CH O); 6.9 (s, 1H, NH);
BX
7.4 (m, 7Harom); RMN 13C (CDCl3,TMS): δ = 17.0 (s, C1); 20.7 (s, C2);
33.6 (s, C5); 71.1 (m, C4); 127.6–137.3 (m, Carom); 148.2 (s, C3); RMN 19
F
(CDCl3,CFCl3): δ = −81.6 (t, 3F, CF3); −120.7 (m, J = 286.0 Hz, 2F,
FF
CF2(1)); −122.1 (m, 2F, CF2(2)); −122.6 (m, 6F, CF2(3−5)); −123.5 (m, 2F,
CF2(6)); −126.9 (m, 2F, CF2(7)). HRMS: M+ calcule´e 813.0511, trouve´e
813.0538.
N-(2,4,6)-Trichlorophe´noxysulfonylcarbamate de
1-Tride´cafluorooctyl-2-thiophe´nyl-e´thyle (2i)

192
I. Chehidi et al.
P. F.: 110–111◦C; IR (CHCl3), υ(cm−1): 3374 (NH); 1763 (C O); 1384
et 1173 ( SO2); 1300–1100 (CF); RMN 1H (CDCl3, TMS): δ = 3.25
3
(syst AB, J = 14.0 Hz, J = 10.5 Hz,3 J = 4.6 Hz, 2H, SCH2 );
AB
AX
BX
5.42 (m, 1H, CH O); 7.27 (m, 7Harom); 8.21 (s, 1H, NH); RMN 13C
(CDCl3,TMS): δ = 33.6 (s, C3); 71.4 (m, C2); 128.2-148.1 (m, Carom);
156.2 (s, C1); RMN 19F (CDCl3,CFCl3): δ = −81.2 (t, 3F, CF3); −120.4
(m, J = 285.0 Hz, 2F, CF2(1)); −122.3 (m, 2F, CF2(2)); −123.1 (m, 2F,
FF
CF2(3)); −123.8 (m, 2F, CF2(4)); −127.2 (m, 2F, CF2(5)). HRMS: M+ cal-
cule´e772.8936, trouve´e 772.8967.
N-(2,4,6)-Trichlorophe´noxysulfonylcarbamate de
1-Heptade´cafluorooctyl-2-thiophe´nyl-ethyle (2j)
P. F: 119–120◦C; IR (CHCl3), υ(cm−1): 3364 (NH); 1777 (C O); 1402
et 1172 ( SO2); 1300–1100 (CF); RMN 1H (CDCl3, TMS): δ = 3.20 (syst
3
AB, J = 14.0 Hz, J = 10.5 Hz,3 J = 4.6 Hz, 2H, SCH2 ); 5.45
AB
AX
BX
(m, 1H, CH O); 7.3 (m, 7Harom); 8.15 (s, 1H, NH); RMN 13C (CDCl3,
TMS): δ = 33.6 (s, C3); 71.4 (m, C2); 128.3–142.3 (m, Carom); 156.3 (s, C1);
RMN 19F (CDCl3,CFCl3): δ = −81.6 (t, 3F, CF3); −120.7 (m, J = 286.0
FF
Hz, 2F, CF2(1)); −122.0 (m, 2F, CF2(2)); −122.6 (m, 6F, CF2(3−5)); −123.5
(m, 2F, CF2(6)); −126.9 (m, 2F, CF2(7)). HRMS: M+ calcule´e 872.8872,
trouve´e 872.8897.
1-Tride´cafluorooctyl-2-thiophe´nyle´thylcarbamate (2k)
P. F.: 127–128◦C; IR (CHCl3), υ(cm−1): 3457 et 3353 (NH2); 1778
(C O); 1300–1100 (CF); RMN 1H (CDCl3, TMS): δ = 3.25 (syst AB, J
AB
= 14.5 Hz, 3 J = 10.0 Hz,3 J = 4.5 Hz, 2H, SCH2 ); 4.77 (s, 2H,
AX
BX
-NH2); 5.46 (m, 1H, CH O); 7.30 (m, 5Harom); RMN 13C (CDCl3, TMS):
δ = 33.5 (s, C3); 69.2 (m, C2); 127.6 (m, C7); 129.6 (s, C6); 131.3 (s, C5);
134.3 (s, C4); 154.5 (s, C1); RMN 19F (CDCl3,CFCl3): δ = −81.3 (t, 3F,
CF3); −120.7 (m, J = 293.0 Hz, 2F, CF2(1)); −123.4 (m, 2F, CF2(2));
FF
−124.5 (m, 2F, CF2(3)); −124.9 (m, 2F, CF2(4)); −127.1 (m, 2F, CF2(5)).
HRMS: M+ calcule´e 515.0224, trouve´e 515.0251.

Sulfonylcarbamates de 1-F-Alkyl-2-Thiophenylethyle
193
1-Heptade´cafluorooctyl-2-thiophe´nyle´thylcarbamate (2l)
P. F.: 144–145◦C; IR (CHCl3), υ(cm−1): 3455 et 3354 (NH2); 1778
(C O); 1300–1100 (CF); RMN 1H (CDCl3, TMS): δ = 3.22 (syst AB,
J
AB = 14.5 Hz, 3 JAX = 10.0 Hz,3 JBX = 4.5 Hz, 2H, SCH2 ); 4.85 (s, 2H,
-NH2); 5.51 (m, 1H, CH O); 7.30 (m, 5Harom); RMN 13C (CDCl3,TMS):
δ = 33.5 (s, C3); 69,2 (m, C2); 127.6 (s, C7); 129.6 (s, C6); 131.4 (s, C5);
134.2 (s, C4); 154.4 (s, C1); RMN 19F (CDCl3,CFCl3): δ = −81.6 (t, 3F,
CF3); −119.7 (m, J = 298.0 Hz, 2F, CF2(1)); −122.6 (m, 8F, CF2(2−5));
FF
−123.7 (m, 2F, CF2(6)); −126.9 (m, 2F, CF2(7)). HRMS: M+ calcule´e
615.0160, trouve´e 615.0186.
REFERENCES
[1] T. Suzuki, K. Yaguchi, T. Suga, and Y. Nagakawa, Environ. Toxicol. Pharmacol., 3,
167 (1997).
[2] Y. Nakagawa, K. Nakajima, and T. Suzuki, Toxicology, 200, 123 (2004).
[3] Y. Wang, L. Li, Z. Tian, W.Jiang, and J. W. Larrick, Bioorg. Med. Chem., 14, 7854
(2006).
[4] A. Battaglia, E. Baldelli, E. Bombardelli, G. Carenzi, G. Fontana, M. L. Gelmi, A.
Guerrini, and D. Pocar, Tetrahedron, 61, 7727 (2005).
[5] M. P. Hay, W. R. Wilson, and W. A. Denny, Tetrahedron, 56, 645 (2000).
[6] A. Gopalsamy, H. Yang, J. W. Ellingboe, H. R. Tsou, N. Zhang, E. Honores, D. Powell,
M. Miranda, J. P. Mcginnis, and S. K. Rabindran, Bioorg. Med. Chem. Lett., 15, 1591
(2005).
[7] J. Clayden, N. Greeves, S. Warren, and P. Wothers, Chimie Organique (Editions de
Boeck, Paris, 2003), Chap. 53, pp. 1482–1483.
[8] M. Be´ji, H. Sbihi, A. Baklouti, and A. Cambon, J. Fluorine Chem., 99, 17 (1999).
[9] M. El Kateb, M. Be´ji, and A. Baklouti, J. Fluorine Chem., 81, 139 (1997).
[10] H. Sbihi, M. Be´ji, and A. Baklouti, J. Fluorine Chem., 105, 103 (2000).
[11] M. El Kateb, M. Be´ji, and A. Baklouti, J. Fluorine Chem., 94, 119 (1999).
[12] H. Sbihi, M. Be´ji, and A. Baklouti, J. Fluorine Chem., 115, 161 (2002).
[13] H. Rmedi, M. Be´ji, and A. Baklouti, J. Soc. Chim. Tunisie, 7, 37 (2005).
[14] M. Hedayatullah and M. Be´ji, Bull. Soc. Chim. Belg., 97, 219 (1988).
[15] M. Be´ji, The`se d’Universite´ Paris VII (1987).
[16] G. Lohaus, Chem. Ber., 105, 2791 (1972).
[17] M. Hedayatullah and J. F. Bault, C.R. Acad. Sci., C285, 153 (1987).
[18] C. Coudures, R. Pastor, S. Szonyi, and A. Cambon, J. Fluorine Chem., 24, 105 (1984).