Chemistry Reference
In-Depth Information
(a)
Ar
H
+
O=P(R
2
)
3
136 RH
Y = P(R
2
)
3
R
1
H
H
O
-
(b)
ArCHO
Ar
R
1
Ar
H
C
-
Y
+
O
S(R
2
)
2
+
H
R
1
Y
+
Y = S(R
2
)
2
R
1
H
H
Ar
H
N(R
3
)
2
(c)
NR
2
+
O
N(R
3
)
2
N(R
3
)
2
R
2
R
1
H
Y =
N
N(R
3
)
2
Scheme 4.41 Schematic reaction profiles of phosphonium, sulfoniumand guanidiniumylides
with aryl aldehydes
R
H
H
13
C
6
Me
I
-
X
-
H
11
C
5
C
5
H
11
C(CN)
3
-
N
+
N
+
N
+
Me
Me
Me
Et
Pr
Me
N
N
N
N
N
N
Me
Me
Et
Pr
Me
Me
R = H, X = MeCH(OH)CH
2
CO
2
R = H, X = MeCO
2
R = H, X = CF
3
CO
2
R = Bu, X = MeCO
2
(
27
)
Figure 4.7
Structures of guanidine-derived ionic liquids
Table 4.17
Azidation of alkyl halides with TMGA (28)
N
+
H
2
N
3
-
refulx
Me
Me
R-X
+
R-N
3
N
N
CHCl
3
Me
Me
28
Run
R
X
Time (min)
Yield (%)
1
Ph(CH
2
)
2
Br
90
100
2
PhCH
2
Cl
60
91
3
Me(CH
2
)
5
Cl
240
60
4
EtO
2
CCH
2
Cl
60
89
5
Ph
2
CH
Br
60
81
