Phosphorus-containing derivatives of indole and pyrole (review). (англ
.).pdf
POCl3 |
P O |
1d
N
H 3
118
> # $" #6$ -#.7$
-'
ClP(Z)RR''' |
P(Z)R'R'' |
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ClP(Z)R'R'' |
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1d |
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N |
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(Z)PRR''' |
H |
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120a–e |
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119a,b |
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!!! 0 ) !!! 0 ) ! !! 0
! !! 0 ! !! 0 ) ! !! 0
! !! 0 )
% % 4#$
% " " "
. (.I1
#$ &
#6; G ;RRR G 13 1 T G 7<6; G ;RRR G 7H T G 7<6 ; G ;RRR G 4 T G 7$
" "
& % % "
4# D$ " "
& # .I1$
! #.$
'
N P(Z)R
1a Cl2P(Z)R 2NEt3
2
121a–c
0 0 ) 0
@ ! 0 , ( + "
&-" ,
2 D 2 * % % "
! 2 #%$ #..$ 2 #%$*
#./$+ , '
-0
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1. PCl5, 2. SO2 |
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R |
3. H2O |
R |
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CH=CH2 |
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CH= CHP(O)(OH) |
2 |
R = H, C(O)CF3 |
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122 |
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1. PCl5, 2. SO2 |
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C(O)Me |
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ClC= CHP(O)Cl2 |
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123 |
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- 02" ? & # *$" % % 4#$
4 26; ; & "
.0
SP(Z)RR'
ClP(Z)RR' |
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45 |
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NEt3 |
N |
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H |
124
Z = O, S, R,R' = Alk, OAlk
4# D$ #
$3 " % .2% " !
% *
S P(O)CH
Cl2P(O)CH=CHOEt
45
NEt3
N
H 2
125
" - 02 1
#$ .3 - 03 1"
4#$! * .4" "
!-?.
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SPRR' |
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S |
S |
S |
S |
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45a,b |
46a,b |
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N |
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H |
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) |
! |
2 |
126 |
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127 |
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2 % "
! .5# .6$# /7$? '
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2PCl5 |
+ – |
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NCH=CH2 |
NCH=CHPCl3PCl6 |
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SO2 |
128 |
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Et4NI |
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NCH=CHP(O)Cl2 |
NCH=CHPCl2 |
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129 |
130 |
-0?
@ ! " 2 ??
2 2 ! # / $'
2 |
NK |
+Cl2P(O)Ph |
N P(O)Ph |
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2 |
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131 |
-?
" /.?-&-13
" // ? '
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CH2 |
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PPh3 |
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Cl2PPh3 |
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N |
O |
N |
O |
Et |
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Et |
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132 |
CH=PPh3 |
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Me |
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Cl2PPh3 |
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R |
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R |
Me |
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Me |
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133 |
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2 % % /0 ?(?+? ! /2 ?/
? ! /3?0 "
'
R |
R |
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ClP(Z)R'R'' |
NH |
NP(Z)R'R'' |
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:B |
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134–136 |
0 ) ! !!$ 0
! !! '1.$$*-,. 0 ! !!
?"
. (I1 ?, #?$ # /4$
#?$# /5$" '
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O |
O |
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O |
O |
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3 |
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3Cl2P(O)Me |
+ |
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NH |
NP(O)MeCl |
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NP |
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O |
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:B |
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137 |
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Me |
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2 |
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138 |
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2 # 3 ! &$ ! "
/6 -. 07 - -? 0 --'
-0-
NCHROH |
ClP(Z)R'R'' |
NCHROP(Z)R'R'' |
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:B |
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139, 140 |
139 Z = S, R = H, R', R'' = OAlk, Alk;
140 Z = O, R = CCl3, R',R'' = OAlk, Alk
NCH2CH2OH |
HP(O)(OR)2 |
NCH2CH2OP(O)(OR)2 |
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CCl4, NEt3 |
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141 R = Alk |
2 % % & ?
" 0. - 0/ -( % " % %
?00 -+ '
P(R'n)F4–n
R |
R = H |
NH |
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NSiMe3 |
P(R'n)F4–n |
R |
142 |
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R |
R = Me |
R |
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NP(R'n)F4–n
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R |
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143 |
O |
O |
NSiMe3 |
ClP(O)R2 |
NP(O)(OR)2 |
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144 |
02 -/ '
COOH |
C(O)Cl |
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(ClCO)2 |
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NBz |
HP(O)(OR)2 |
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NBz |
NBz |
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–CO, –HCl |
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(O)P(OR) |
(O)P(OH)2 |
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2 |
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1. H2/Pd |
NH |
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NBz |
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2. H2O |
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145 |
-0
% %
/ . ( : * < ) < + , * 9
% E % % E * # -*$" ! %-, 6
"03% % " %
? '
-0
NNHR'
O
R
146
! ) ) 2 3
% " -
* - 04 3 * !
" % "
CH=NNHC(O)(CH2)nP(O)R2
H2NNHC(O)(CH2)nP(O)R2
47a
N
H
147
/ / * + ( : * < ) ? < < ( ( % =( * * , * ) (
%- 04 1 06 1"
% " ( / "
*
2 ? #$* * ? #$* *
- #041$ " %
"-
" " % % 05 06 4 7 0 , '
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CHC(O)R' |
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+ |
R'' P(O)O– |
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O |
2 |
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49a,b |
R'C(O)CH2P(O)R'' |
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R |
C(O)R' |
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C |
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P(O)R''2 |
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O |
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R |
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149 |
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CH=CHC(O)R' |
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R'C(O)CH2P(O)R''2 |
N |
+ |
R''2P(O)O– |
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47a,b |
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R |
C(O)R' |
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CH=C |
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P(O)R''2 |
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N |
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148 |
R |
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+ 4 '5+. 1 ,* 56 ,
'7 ,6 8-56* . '7 ,6* 56* . "#
-0(
" -? 06
-+-0F " " + 0F
" 4 7
27 " !
% " (. '
CH2 |
C(O)OMe |
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P(O)(OMe) |
P(O)(OMe) |
1. NaBH4 |
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47b |
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C(O)OMe |
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1. TiCl4 |
2. Et3N, t |
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2. O |
N Me |
Ac |
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1. Ph2P(O)N3 |
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P(O)(OMe) |
2. PhCH2OH |
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C(O)OH |
*$ |
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_ |
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P(O)(OH)O |
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Ac |
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+ |
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NH3 |
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Ac |
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150 |
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/ 0 * + ( @ # $A: * < ) 8 % =( * # $
-42" *- 0 * % (? ( '
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P |
OR |
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R'' |
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R''Cl |
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4a |
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N R' |
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151 |
H |
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$ '$"# ! !!
6 % % % %2.(? '
+ _ PPhRR'X
N
H
152
"$ '$ ! /' ,-
!2/% % 4#$ 0
/ '
P(OR)2Cu2Cl2
N
H
153
-0+
/ 2 + = * * % + ( : * < )
> % *
-# & ! %$ 20 " &
% %22*23/ '
ClP(O)(OR)CH=CHOR |
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(O)P(OR)CH=CHOR |
1d |
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Cl2P(O)CH=CHOR |
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N |
ROH |
154 |
H |
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H 0 " 20 3 " " ! " @6)
22( ? *23'
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(O)P(OR)CH2CHO |
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N |
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H2NNHC6H3(NO2)2 |
O2N |
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155 H |
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(O)P(OR)CH2CH= 
NO2
N
156H
20 # . (I1$
24'
(O)P(OR)CHBrCHBrOEt
N
H
157a,b
a R = Et, b R = Pr
(-" % %
! " ( #25$ -
#26$" 4#$ * %
" ! " ((
"-%
C(O)CH2Cl |
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ROPR'R'' |
(O)CCH2P(O)R'R'' |
N |
158 |
H |
(O)CCH2P(O)R'R'' |
N
H
159
-0/
9 %
! ? ( # +. /.I1$ "
+ 2 #$ 256 EM &
2 +.
% % 37 3
(+
Me |
O(O)PMe |
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Me |
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HO |
N |
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H |
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H |
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N |
160 |
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H |
Me |
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O |
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Me |
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_ |
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+ Cl |
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(Me)3NCH2CH2 O |
H |
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(O)P |
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N |
161 |
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H |
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/ 3 ( : * < * ) & * + )
3 E E &
% +
" % % +( +0
* % % %-23. -
23/ -230
1a |
+ |
+ ClP(O)RR' |
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P(O)RR' |
N |
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N |
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H |
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N |
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162 H |
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H |
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H |
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N |
RR'(O)P |
N |
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RR'P(O) |
N |
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N |
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163 |
H |
164 |
H |
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% " 2 "
% 4 % J
& % &
% " "
-00
+/ % " *
& 3. "
& #$
0 % % B ! ! ' ! ' ; ? :% ! ! ! !& ' !&
'
* " ?
+, 7 ) +, /. / * % /?
/- 32
* ,+-4 *33" " /
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O |
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HN |
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H2NNHPh |
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P |
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P |
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Ph |
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165 |
Ph |
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Ph |
H2NNHPh |
Ph |
P |
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P |
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O |
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N |
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H |
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166 |
* ! * ?34
) /( '
R' |
R' |
R |
CH2R |
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NHN=CP(O)(OEt)2 |
N |
P(O)(OEt)2 |
R'' |
H |
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R'' |
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167 |
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7 /+ " // /, 35% %
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(CH2)nP(O)R(OR') |
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NHN= CH |
N |
(CH2)n–1P(O)R(OR') |
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H |
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R'' |
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R'' |
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168 |
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* *35&
- 36" *35
9- ? " & "-. 0. 0? ?-
" % /0 /, % " 0
? * " %
* * ? "
-0,
H! % - ? " 1 E13 4# D$
#36 35$ 1 E4# D$ # .7 36$ 1 E4#$ #01 47$ " %
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CH2P(O)(OR)2 |
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N |
ZnCl , 180 oC |
N |
CH2P(O)(OR)2 |
H |
2 |
H |
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69 |
P(S)(OPr-i)2 |
168 |
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N |
CF3COOH |
N |
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P(S)(OPr-i)2 |
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H |
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H |
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120 |
PPh2 |
169 |
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N |
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N |
PPh2 |
H |
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H |
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46b |
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170 |
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"- ? ? ! 34 "* * !2 *
# $ ! ? ! #/+ U G 6 ; G 3 ; G 4#7H$ $" # M$'
N(CH3)N |
AcOH |
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(A) |
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P(O)(OEt)2 |
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Me |
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167 |
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3 26; 34" # M$"
& -? 4 )
* " & *
" 0-'
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NHNH2 + (RO)2(O)PC(O)CH2 |
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R' |
R'' |
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R' |
R'' |
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P(O)(OR)2 |
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171 |
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" ?-! -?
-& ? 0
" % 0( 0+ 4.
* * ! @ !
* * % : M #1 7
?..I1$ ? ! < 8 #471 * 0.I1$ ? 0/
-,.