Diels-Alder Approach to Biaryls (DAB): Importance of the ortho-Nitro Moiety in the [4+2] Cycloaddition.
Bradley 0. Ashburn and Rich G. Carter* Department of Chemistry, Oregon State University, Cowallis, OR 97331.
Electronic Supplementary Information: Spectral Data
Supplementary Material for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2008
Diels-Alder Approach to Biaryls (DAB): Importance of the ortho-Nitro Moiety in the [4+2] Cycloaddition.
Table of Contents
N . o m VI. P 4 V I w w
N m N ' " W 0 IDm. 00,". m . O W V I ~ N
0 0 . P N V I w N O O N O V I O l N W x z g r n x x m N N 2 z- -- - - T-.
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O W m v w - l r W N N W X P O 7 0419 I P . cl C m W w o O W g W m O x o P w m "
S3
2-nitrophenylacetylene + Me0 diene Current Data Parameters NAME BOA1176 EXPNO 2 PROCNO 1 DU USER
/m brada
F2 - Acquisition Parameters Date- 20070731 Time 14.30 INSTRUM DPX4OO PROBHD 5 lrml BBO BB-1H PULPROG Zg~g30 TD 65536 SOLVENT NS 996 DS 4 SWH 25125.629 Hz - ~~ FIDRES 0.383387 HZ AQ 1.3042164 sec RG 9195.2 DW 19.900 usec
6 .OO usec 299.2 K
0.15000001 sec 0.03000000 sec
DELTA 0.05000000 sec TDO 1
P1 PL1 SF01 100.5936591 MHz
CPDPRG2 waltz16 NUC2 1H PCPD2 135.00 usec PL2 17.40 dB PL12 17.40 dB PL13 17.40 dB SF02 400.0116000 MHz
F2 - Processing parameters SI 32768 SF 100.5825950 MHz WDW EM SSB 0 LB 3.00 Hz GB 0 PC 1.40
S4
2-nitrophenylacetylene + 2-TMSO diene
Current Data Parameters NAME BOA1 17 0 EXPNO 1 PROCNO DU USER
F2 - Aca Date- Time INSTRUM PROBHD PULPROG TD SOLVENT
FIDRES
TE Dl TDO
1 /m
brada
lisition 20070730 Parameters
15.14 DPX4OO
5 mm BBO BB-1H zg30
32768 CDC13
22 2
6410.256 Hz 0.195625 Hz
2.5559540 sec 322.5
78.000 usec 6 .OO usec
298.2 K 2.00000000 sec
1
-------- - - - - - - - - CHANNEL fl I==='== NUC 1 P1 14.70 usg PL1 0.00 dB1 SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF 400.0100000 MHz WDW no SSB 0 LB 0.00 Hz GB 0 PC 1.00
S5
P 0 0
m-2-2-2vl " "r r f , P P W P W W N O . . . . N I I O P P P O P W ,I o o o o o x m 11
ZgigigiE i! N 0 I1 n II
GIII I I I IXCC a x x m m m 111111 m N N P n n n e m n n n - 111
S6
2-nitrophenylacetylene + MeO/OH diene Current Data Parameters NAME BOA1177 EXPNO 1 PROCNO 1 DU /m USER brada
F Z - Acquisition Parameters Date- 20070731 Time 15.18
INSTRUM PROBHD 5 mm BBO DPX4OO BB-1H PULPROG zg30 TD 32768 SOLVENT CDC 13 NS 3 2 DS 2 S WH 6410.256 Hz FIDRES 0.195625 Hz AQ 2.5559540 sec RG 512 DW 78.000 usec DE 6.00 usec TE 299.2 K Dl 2.00000000 sec TD 0 1
NUCl 1H P1 14.70 use< PL1 0.00 dB SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF mw SSB LB 0.00 Hz GB 0 PC 1.00
S7
~ g E E ~ ~ ~ ~ "a " " " w r 4 aLzcszgi! N W u g N W I 1 5EZz5 v -11 g E E E 3 E 2 2 s Z $ Z 5 g G 2 s E Z F Z r0rn.n c u a m z 2 gcE$$5
a !a 11 10 9 g $ Z E : ~ Y ~ '2 II I, . I1 2 * F 30 : m 0 0 0 m C. I
m F P. P 3 :. L 0 3 0 0 s p P N a . O m :i'
V I W V I W - C m o o o r ~ o w ~
N W N F C C C W "N W I C O O O N W V I P r n V I m:w8"z% $ " W $"$ m-J-J-Jm " m - 4 . . O O O W m . W N W . F V I D W X V I Z N 5 2% 0. . . . N I1 V I . . Fll 0 0 0 W ' W - J F W m VI VI19 1 P . r m z ~ E ~ E K E tgFw:l m I
0 It 0 II 0 0
S8
2-nitrophenylacetylene + BnO/TMSO diene
Current Data Parameters NAME BOA1181 EXPNO 2 PROCNO I DU USER
/m brada
F2 - Acquisition Parameters Date- 20070803 Time 14.04 INSTRUM DPX400 PROBHD 5 mm BBO BB-1H PULPROG TD SOLVENT NS DS 2 S WH 6410.256 Hz FIDRES 0.195625 Hz A0 2.5559540 sec
Dl TDO
- - - - - - - - -------- CHANNEL fl =I====== NUCl 1H P1 14.70 usec PL1 0.00 dB SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF 400.0100000 KHz WDW SSB LB GB PC
S9
2-nitrophenylacetylene + BnO/TMSO diene Current Data Parameters NAME BOA1181 EXPNO 4
BnO
d m m m -3 0 P e . . . . P P W O P P P P
PROCNO 1 DU /m USER brada
F2 - Acquisition Parameters Date- 20070803 Time 15.01 INSTRUM DPX4 0 0 PROBHD 5 nun BBO BE-1H PULPROG Zg~g30 TD 65536 SOLVENT NS 1918 DS 4 S WH 25125.629 Hz FIDRES 0.383387 Hz A0 1.3042164 sec RE 5792.6 DW 19.900 usec DE 6.00 usec TE 298.2 K Dl 0.15000001 sec dl1 0.03000000 sec DELTA 0.05000000 sec TDO 1
7.80 usec -3.00 dB
100.5936591 MHz,,
CHANNEL f......... waltz16
1H 135.00 usec
.-- PLl2 17.40 dB PL13 17.40 dB SF02 400.0116000 MHz
F2 - Processing parameters SI 32768 - - SF WDW SSB LB
100.5825950 MHz EM
n
S10
Current Data Parameters NAME BOA1178 EXPNO 1 PROCNO DU USER b r a ~ i ~ l lill 1 F2 - Acquisition Parameter Date- 20070801 I Time 15.38 INSTRUM DPX400 PROBHD 5 m BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDC13 NS 3 2 DS 2 S WH 6410.256 Hz FIDRES 0.195625 HZ AQ 2.5559540 sec RG 1149.4 DW 78.000 usec
- - - - - - - - -------- CHANNEL fl =======r NUC 1 1H PI 14.70 usec PL1 0.00 dB SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF 400.0100000 MHz WDW no SSB 0 LB 0.00 Hz
I " " I ' " ' I ' " ' I " " I ' ~ " I " " I " " I " " I ' " ' I - " " 1 " " I " ' ~ ~ ' I " " I " " l ~ ~ " l " ~ ~ l ' ~ ~ ' l ~ ~ " l " ~ ~ l
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 '1.5 1.0 0.5 0.0 ppm
S11
Current Data Parameters NRME BOA1178 EXPNO 2 PROCNO 1 DU /m USER brada
F2 - Acquisition Parameters Date- 20070801 Time 15.43 INSTRUM DPX4OO PROBHD 5 mm BBO BB-1H PULPROG zgpg30 TD 65536 SOLVENT NS 1768 DS 4 s WX 25125.629 Hz FIDRES 0.383387 Hz AQ 1.3042164 sec , RG 4597.6 Dw 19900 usec 1 ! DE 6.00 usec TE 298.2 K Dl 0.15000001 sec ' ' dl 1 0.03000000 sec DELTA 0.05000000 sec TDO 1
NUCl 13C PI 7.80 usec PL1 -3 .OO dB SF01 100.5936591 MHz
- -------- - - - - - - - CHANNEL f2 ======== CPDPRG2 waltz16
Z i 2 1H
135.00 usec PLZ 17.40 dB PLl2 17.40 dB PL13 17.40 dB SF02 400.0116000 MHz
F2 - processing parameters SI 32768 SF 100.5825950 MHz WDW EM SSB 0 LB 3.00 Hz
S12
:I ?.05,".
g! my: -
m .
a L s:
L :! :: ZL
SL 0 :
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in:
A
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z t 8 L u . u 3 '
S13
mlo'd'dlo w r r r o Z 3 1 1 O W W N ' d O U l l N W N Z N ' d l l
0 11 8 11
0 . I w rn W I W m u 4 m . . WII w o m w 11 W O O 0 11
p E g ii n I1
YI
0 0 0 . . . 0 0 W W N . o m m u m W. W 0 0 0 W N O W N N 0 O'd O O O N w w + m m n m a a w w r 4 o o o o w m . ~ N W . rum^ W X P O M
~ o o ~ N o o ~ ~ ~ ~ P N w ~ o ~ o ~ ~ ~ m m m x e e a x x m m m v l v l r n ~ ~ ;d n n o m m n V1 o n
S14
3-nitrophenylacetylene + Me0 diene Current Data Parameters NAME BOA1182 EXPNO 2 PROCNO 1 DU /m USER brada
F2 - Acquisition Parameters Date- 20070806 Time 13.07 INSTRUM DPX4OO PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3
DS S WH FIDRES AQ RG DW DE TE Dl TD 0
6410.256 Hz 0.195625 Hz
2.5559540 sec 181
78.000 usec 6.00 usec
299.2 K 2.00000000 sec
1
Nuc 1 PI PL1 0.00 dB SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF 400.0100000 MHz WDW no SSB 0 LB 0.00 HZ GB 0 PC 1.00
S15
x $ s ~ e o g z g ~ ~ a z a ; : ; y z i q o r r ~ v o u II o r r m g I N W N UN-11 C r O 3
v I1 P 0 I1 I, B m Cn z. E m r P. ID w
0 3 0 0 1 9 0 r N v
o o r . o m C n U 0 mwLn C( W . r i w 1 r n o o o r d o w w r W
N w w r r r r w r N w l r o o o N w w - m w m $! o o o w m . W N W . r u m ~ m x w ~ w w . . s g ? I , I 0 0 0 1 0 . w m r w m WOmQ , I D .
P 0 r m
E $ 2 $ E g g 4 / / $5 / / $ b $ " 5 5 $ g g m n II B n II - n n
-- - -- - - -
S16
4-nitrophenylacetylene + Me0 diene
Current Data Parameters NAME BOA1181 EXPNO 1 PROCNO 1 : # DU USER bra;: I ,I 1 F2 - Acquisition Parameter Date- 20070726 , Time 16.33 INSTRLlM DPX300 PROBHD 5 mm QNP 1H/1 PULPROG zg30 TD 32768 SOLVENT CDC 13 NS 3 1 DS 2 S WH 4789.272 Hz FIDRES 0.146157 Hz AQ 3.4210291 sec RG 362 DW 104.400 usec DE 6 .OO usec TE 298.2 K Dl 2.00000000 sec TD 0 1
PI 9.06 usec PL1 -3 .oo dB SF01 300.1321009 MHz
F2 - Processing parameters SI 32768 SF 300.1300000 MHz WDW no SSB 0 LB 0.00 Hz
S17
P 0 0
m d d d m fl
I e C s: C C C P W P N
O . . . . N I , O L P P O P C I1 0 0 0 0 0 x m !!
0 :: I 10 m W I C m w d UI.. PI1 1 0 0 m w 1 1 C O O 0 !!
s p 2 peeeg peg 1 : : : x z 6 :$E m r( 0 0 0 m m n VI n II n 11 n n
S18
S19
3-nitrophenylacetylene + 2-TMSO diene Current Data Parameters NAME BOA1188 EXPNO 3 PROCNO 1 DU USER
/n brada
F2 - Acquisition Parameters Date- 20070804 Time 7.53
PROBHD 5 mn QNP 1H/1 PULPROG ZgP930 TD 65536 SOLVENT CDC13
DS 4 S WH 18832.393 Hz FIDRES 0.287360 Hz AQ 1.7400308 sec RG 16384 DW 26.550 usec DE 6.00 usec TE 298.2 K Dl 0.15000001 sec dl 1 0.03000000 sec DELTA 0.05000000 sec TDO 1
- - - - - - - - -------- CHANNEL fl ===n==== NUC 1 13C PI 8.80 usec
-3.00 dB 75.4760505 MHz I / 1
- - - - - - - - -------- CHANNEL f2 CPDPRG2 waltz16 NUC2 1H PCPD2 80.00 usec PL2 -3.00 dB PL12 17.55 dB PL13 17.55 dB SF02 300.1312005 MHz
F2 - Processing parameters SI 32768 SF 75.6677490 MHz wDw SSB LB GB
S20
A . L 0 - 0.94 o . - .
s l I
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r 0 8 1 ZwR K r 2 z 2 2 2 * m
0 - m . W m . U N N W X V I o W 6 r n gOS$ Z p P . o m . om,,, L?," , P . m b o o m m o o 4 r o o . o o c l ~ ~ m N m m w r o o o $ o o o o o o m g r o o m o ~ O N O O N O ~ ~ N P O ~ O ~ O ~ ~ ~ & 2 r w z 2
-.- r. - - ----; ,, ,, X R -- - - - - S21
4-nitrophenylacetylene + 2-TMSO diene w P m m c v m w ~n rl rlrl . . . . . . . O P r l L n m m P w Ln
m m ~ q w TJ TJ
rl flflflfl rl
rl rl rlrlrlrl 4
Current Data Parameters NAME BOA1179 EXPNO 5 PROCNO 1 DU /m USER brada
F2 - Acquisition Parameters Date- 20070803 Time INSTRUM DPX4OO PROBHD 5 mm BBO BB-1H I 1 '1 PULPROG zgPg3 0 TD 65536 SOLVENT NS 1501 DS 4 S WH 25125.629 Hz FIDRES 0.383387 Hz A0 1.3042164 sec
2048 19.900 usec
6.00 usec 298.2 K
0.15000001 sec - - dl 1 0.03000000 sec DELTA 0.05000000 sec TD 0 1
NUC 1 13C PI 7.80 usec PL1 -3 .oo dB SF01 100.5936591 MHz
- - - - - - - - -------- CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 135.00 usec PL2 17.40 dB PL12 17.40 dB PL13 17.40 dB SF02 400.0116000 MHz
F2 - Processing parameters SI 32768 SF 100.5825950 m z WDW SSB LB GB
S22
E E B g Z 2 m = I
w 2 m u
% ; 0 14
E 2 O W Y
P 823 o ~ o m m 0 0 0 o m -
s $ %
% {
Z!
m g j ma :
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E . a l
Ur3UtlL. r m m = 0 0
N
0 N
0 (n 0 4 ( n O N m w ( n o w m . m w O W . O W L " 0 . 0 0 . P O N O O W O C C u m u u m n 44 n
U I .
2 . 2'
1.13 - K i % I g! Pi 0 . w . K {
I x l P l 0 .
-L
in
A
0:
s I s: - 0 . -0 3 '
S23
x s ~ z s ~ c z 3 ; ~ ; g g g : : 3 ~ ~ 9 : ; gFFEs:gssgg:ssgazgs;z s z g ~ ~ ~ W E I N W N E N V O P P U
L 11 V
I# P 3 s e s a c , I E ~ i 6 $ a 0 . GI I1 N I1 : 11
m 62
m m C. !2 g !. E r g L o l s 0 P N m c w
0 0 P . o m m :a m u 0 m w m W. C. m w r P 2 Z m o o o r m o w w ti
C . C P C . W C.N W I P O O O N W - J P m m . m z W g W ? z I- 0 %g m 4 4 4 m r? m u 4 . . OOOw.m. w N W . m Z ) m X W O t i a ,, E O + o a m m o ~ L L L ~ P E : ZbLL!: 8g8%gNE%E S Z 9 L g L 6 $ ' c. m O O O O O O ~ ; O O O O O Z ~ I ~ P O O ~ I I I - o o I - ~ o o m P - ~ w P . , m o z o ~ m m &SwN:L'
: ;askeg i peg j ;;;YE 8:: ID 0 I1 0 I, 0 0
m
S24
0 'A ?. YI g 111
L. P. L. 9 ; w z g X mm Nos z b a o r Z - r w r m 0 0 0 O W - N r c O N m m m o
C 0 O N W O P o w m . ~ K ~ E E : : ? K a l z: b b s8:k Xb;,! Z w b g E E E F ~ 2 % L g b 2 $ P m o o o o o o m p r o o x n r o N o o N o m m N ~ w m o z o r o m E 2 r - 2 2 S25
" L ~ S K Z ~ E E W E ~ : ! ~ 2 ~ s ~ ; ; g:eEsEzsgzgzsggas;zga s z s g Z o o r w I N W N EN'dll C - 1 1 3 % F g Z z g , PI O'dP6
'0 L 11 s r L n z m z & II I, E 3 $ 8 $ ' g 3" 3 :: I1 La
m m P u L n
- P C - 3 ; L O Y 0 o n O I r I r O O P b. N L 'd - o m E N"J g z C r & m w m W. C. N 0 U 0 O'd
C W - - 2 1 Z Z Z Z N CRPZK m s m w u , , 0 0 0 U ) m . W N W . ~ v u x O O V $ L g $ i! i!2 a4>>? c, , ~ ~ y ~ l l O O O w . U ) 4 C . W m m m s C - . ,
Z o k o ! 2 ~ ~ $ 8 6 6 6 Z G K 1 1 E8ZXi , Z Z 8 L 8 Z b 2 Z E C - Z :ZEB:Z% P a p N 2 2 " 2 $ $5 1: W g $ " E $ g E E m 0 I1 0 II 0 0 -
L"
S26
3-nitrophenylacetylene + BnO/OH diene
DU USER
Im brada
F2 Date- - ~cquisitlan 20070804) ~arameke,s !I, 1 Time 16.39 INSTRUM DPX4 0 0 PROBHD 5 rn BBO BB-1H ' ' 1 PULPROG zg30 TD 32768 SOLVENT CDC13 NS 25
FIDRES 0.195625 Hz AQ 2.5559540 sec RG 322.5 Dw 78.000 usec DE 6.00 usec TE 299.2 K Dl 2.00000000 sec TDO 1
NUC 1 1H PI 14.70 usec PL1 0.00 dB SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF 400.0100000 MHz m w no SSB 0 LB 0.00 Hz GB 0 PC 1.00
S27
3-nitrpphenylacetylene + BnO/OH diene m m m ~ d ~ r n m * ~ o m ~ r n w w d F O r n m U l O P W O d O W N d 0 . . , . . . . . . . . . . . . . r - w m r n w m d m m m t - * d d m d m m O ~ ~ ~ ~ N N N N N N N o o d d d d d d d d 4 d d d d d d d
Current Data Parameters NAME BOA1183 EXPNO 2 PROCNO DU USER
1 /m
brada
F2 - Acquisition Parameters Date- 20070804 Time 17.09 INSTRUM DPXIOO PROBKD 5 ran BBO BB-1H PULPROG zgPg30 TD 65536 SOLVENT NS 1204 DS 4 S WH 25125.629 Hz FIDRES 0.383387 Hz AQ 1.3042164 sec RG 4597.6 DW 19.900 usec DE 6.00 usec . - Dl 0.15000001 sec dl1 DELTA 0.05000000 sec TDO 1
NUCl 13C P1 7.80 usec PL1 -3 .OO dB SF01 100.5936591 MHz
CHANNEL f2 =======r CPDPRG2 waltz16 NUC2 1H PCPD2 135.00 usec PL2 17.40 dB PL12 17.40 dB PL13 17.40 dB SF02 400.0116000 MHz
~2 - Processing parameters SI 32768 SF 100.5825950 MHz
SSB LB GB
S28
-
:: s; s l r 3 -i 2 4 5 i 0 .
-i % L K I
g-i
s l z j
i P i U I .
P i 0 .
A
in:
A
0:
s: s: u . u 3 '
E E r 0 OWM . . Z Y D o o z o m m 0 0 0 0 0 om,- ,
N -- 0 . o m 0 Ln P 0 4 W P P O N m w w o n w ' O V O W m . W v l t l N N p ) V r 4 r
~ O N O O N O ~ ~ N W W ~ O X O ~ O ~
S29
4-nitrophenylacetylene + BnO/TMSO diene Current Data Parameters NAME BOA1172
OIOI P O O P O W L ~ W ~ N N N mco m m m ~ d W 0 0 1 m m N 4 . . . . . . . . , , . . . . P W W L n W d O a 2 c o W m r l 03 T-4 m m e e m m m ~ ~ ~ m m o 0 r ld r ldddddr l r l r ld rl rl
w e (q m m o P ~ n , . . . P P W O P P P P
EXPNO 2 PROCNO 1 DU /m USER brada
~2 - ~cquisition Parameters Date- 20070730 Time 15.59
INSTRUM PROBHD 5 mm BBO DPX400 BB-1H PULPROG ZgPg30 TD 65536
F2 - Processing parameters S1 32768 SF 100.5825950 MXz WDW EM
SOLVENT NS 1846 DS 4 S WH 25125.629 Hz FIDRES 0.383387 Hz A0 1.3042164 sec RG 4597.6 DW 19.900 usec DE 6.00 usec TE 299.2 K Dl 0.15000001 sec dl1 0 :03000000 sec DELTA 0.05000000 sec TDO 1
- - - - - - - - -------- CHANNEL fl =.===r== 1 NUCl 13C P1 PLl SF01 100.5936591 M H Z : (III - - - - - - - - -------- CHANNEL f2 =====r.= I PCPDZ 135.60 usec PLZ 17.40 dB PLl2 17.40 dB PLl3 17.40 dB SF02 400.0116000 MHz
SSB LB
S30
phenylacetylene + Me0 diene i ljl o ~ ~ ~ ~ N o ~ ~ ~ N w N P ~ ~ ~ w ~ ~ L ~ ~ L ~ o w ~ ] ~ w L ~ N w ~ c o L ~ ~ ~ ~ L ~ o P O‘I Current Data Parameters ~ ~ ~ ~ ~ ~ ~ ~ P W W ~ ~ ~ ~ ~ O O ~ ~ ‘ I C O C O C O P W W ~ ‘ I ~ ~ ~ ~ ~ \ ~ \ P P W L ~ L ~ ~ ~ W NAME BOA1192 m m m m v v e e e e e e e e e e e e m m m m m m m m ~ ~ r l ~ ~ ~ ~ ~ ~ ~ ~ o 1 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 03 EXPNO 1 P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P P m PROCNO
I DU /m USER brada F2 - acquisition Parameters Date- 20070809 Time 16.35 INSTRUM DPX4OO PROBHD 5 mn BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDC13 NS 19 DS 2 S WH 6410.256 Hz FIDRES 0.195625 HZ AQ 2.5559540 sec RG 161.3 DW 78.000 usec DE 6 .OO usec TE 299.2 K Dl 2.00000000 sec TD 0 1
- - - - - - - - -------- CHANNEL fl ======== NUCl 1H ~ - P1 14.70 usec PL1 0.00 dB SF01 400.0128001 MHz
F2 - Processing parameters SI 32768 SF 400.0100000 MHz WDW no I SSB LB GB PC
S31
m -
"7 z. u VI
L LU " t.. P
8 8 . . . F O O C * N . o m z
" 7 w m W . " N U O W C C I - c w W N W I w O O O N w m c m m m a m ~ r d w ts E! 0 . . 0 . . . . 0 0 0 w m . W N W . N II "7. . WI I o o o w . -41-WO, P W Q I P . E %
g o s , ~ p ~ ~ - g g 2 j 8 1 & g z P P Y ~%~~~~~ g),,;$ I, I, rt
8 n II n 18 n n VI
S32
9': c n .
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P n N P F m o b 0 . . 0 0 4 P I1 II
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0 0 VI 0 4 V I O N m VI 0 - m . 10 0 1 0 . OVlVl 0 . O O C P
C O N O O N O
0 m . P F F 1 0 0 0
VI. u m u O N V I FP m m u m w
P P
S33
w o r m ornrnm3::2 m 4 1
w 8 m m m ' C.
0 3 0 lLI
'" u m L N W M ' W '"N . . - 4 3 2ozogg:;
g p p p X z 0 " O P W N W 0 : N W N E N W I I I\
z 11 8 11
- ~ . . . 0 0 P ' "WUI ? O K W . P 0 0 0 ' \ O O W N O O O N w w l r m ' " 0 0 0 w m . \ O N - . r 0 0 0 w . W Y I ' W r n ' 000- 00. m m ~ P
P 0 0 ' N O O N P - J ~ P W
V I V I r n X C C m m m lorn :$2 m n n n m m n 0 0
1
S34
