Dipolar Cycloadditions of Mesoionic Compounds with 2-tert-Butylfulvenes. A New Route to...
-
Upload
hiroshi-kato -
Category
Documents
-
view
212 -
download
0
Transcript of Dipolar Cycloadditions of Mesoionic Compounds with 2-tert-Butylfulvenes. A New Route to...
4!9P eT e t5 N 2 9 1
@ 1
P S 0 0 4C
D C yo M C w2 - t eA N R t P
a zS tA [ 6C y ca I so A 1
H iK aT oK oa M C
D C S U M
A kK
D C M E E U
W
A bS em c 2 d ++ c f e i
r c a i hi a o a
a t o @
I N T
T d ic y cr eo m ec oh b e xi na
t a n r ea a i ms yr t t c oo m f ih
c l eT ha s eo s tw h s t t c y c lr o m
c o mc b e xt t s yo s ~ s ee in a t ef c
g ah e t es yI i r as ut f t u v r ea t k c
r e ao m e sc ob et [ + 2 m W h r f f t f t
t a f m e sc o1 r w t r2 i a [ + 6 m t g c y3 A t
s t ii w f ot t c y c3 a s ta d n s t p f f m
t iO e aa tt o b[ + 6 c yo m ec w f i
g [ + 2 c y c la lc oo t r em s uo t f o p
d o aw o bw m o t r e aI o ct u t s [ + 2 c
t iw f um b h ib i n to a b s uo t 2 o t f r
a ra a c o na nt h ep o[ + 6 c yo m c w
9
9 H a
f u lm ar e aW a i mt b t u o s u6 -f 4 e a
e l ir e at s [ + 6 c y c5 s a a n s r t a v o c
g ac y c l o p6 w a i s ow a ( p s.
Q + @ — ga
1 2 3
54
- ‘eJa
6
I t p ar e ao s em ec ow 6 - (a 6 -
b u t y9 a 1 a d e sT t t iw s ew t e xt 2
g rs hb b ue nt b t 3 -o f ut i nw m c a a
m o lo d i m ea a ca w b r ee lf t d [ + 6 c
o t he x tp r oF t p uo c ot c yr o a f m
c o mw 2 - t e r t - b u2 w a i nw t h t e t r
t ir ow t i ,d eo g l eg T r eo [ + 6 c ya s
c ef o ro s ep s e ua d eb T f oo c o[ + 2
c y c l o a dp ra i s oo p r[ + 6 c yw t m
c o ma a d e s
R EA D I
2 - t e r t - B u t y9 h b p rb t r o s c y
7 a d i m e td ia cW p rt c ob t ro s t
c l o p ew t 0 -s o d i n td 8 T p ri e st s a t
f t p r eo 6 - ( d i m1 T p ro bi t w w a c 1 : 1 m
o Z a E - i6 - A c e t o1 w p rb a t p f t p
N
P~ N +
M e 2M —
tb
\7 t
9
H C7
8
O
b\
t
1
“
A
“
I
\
t1
A n r t p s e u9
a ro 6 - a c e1 S ot e r t - bw t w e f a t
s os o t f od e r1 t f w d it w a c I t c
o o s t e rw i sb i w n p ot e si g b N o N m
u r e
C y cw 6 - ( d ia 6 - a c e t
T r eo 3 - p h1 w 6 - ( da 6 - a c9 a 1
r e g i og t c y c l o1 i 3 a y r eb s e
s o c ad ia e l io a m oo d i mo a a f t [ + 6 a
d u1 a 1 T p ri n t [ c ]i 1 b i d n s a I N
s ia s st t a dh ya o t c or
P
[
H
N
x
N
J- cf , p ~ —
a
\+ 9 o 1 _
o 0- - H ‘-B” \ \ ~.ph
H1
01 Z = N 1
1 Z = O
$P
AI
-+ 9 o 1 _ t “ ‘
-T
\ \Ph S O- 1
1
X y-2
P2
T m e s2 , 5 -- d i t1 r s iw t d ia t
a c e t o9 a 1 t g t c y c l o1 i 5 a y r ev [ +
6 c y c lT r eo t m et r i p h2 w t d i
v 9 g o a t a mo t e xc y c2 p d t t i o t
o x a z oH ow i w g ei s b t ro f l f1
w t rp h oi t p ro t a m i9 t d i pp 2 c b
i s o( 1
T m e s4 - p h e n y l -2 r w t d i m9 t g
t p r ot w hc y c l o p2 ( a c y c l2 ( s
t uw a so t b o N s pT C a C s o t m [ 2 a
p a 6 1a 1 w t o t m [ ~2 a a ? 1 a 1 r
M o rt s io t H o t [ a l2 i s hd ot 6 b t d e o
t n el -s u bT ht c y ci t c p rl r et
o tr e ad e sa ba g t [ + 6 c y2 a 2 f w e o
9 H a
c ad ia e l io d i mt p t g t t f p
A t p s e ud ea a d c oa t U s p (
E x p ea s it t o a zs ht p ro s d o i nc
t r ai t hm o l
, - +,.,u~]2 2I
I- C - M
‘-’”-”+‘-’u-?2
C y c k xw 2 - t e r t -
T d i m e2 r es lw 3 - p1 A h a t s o
t t c o mf t d i t a 1I o t s y1 w s r a 2 o t d
c y c l o p3 w f oT p oo t f oo o r e3 c b
e l ib N m e as ie n hb t i sm p a H
H a b et t e rp ra H w o bb n r b t t p
a H A p pt r ei t c p ri a [ + 2 m a t c 2 u
d ee x to c ad ia s pd e ht t a r I i i
t n t t s y1 a u nc y cw t i a [ + 2 m W t
r e aw p e ru a i g b la e sa a s r t ( f d
v a ra mo a np ra sa t 2 a , 4d e2 w f i a
u w t d id e r3 H oa ti so t t ed 2 w n
s u cd t i r d e h yt t a r3
T m e so x a t h2 a r ew t d i m2 i a [ + 2 m a
g t c o ni s o3 ( 1b e xo c d f t c y3 a s
n ed e h y dT a po o m I N s a a r eh m f (
1 .i n da s h ie ff t 3 -g a s ut a s 3 r t i
r e g3 I nM c a lp eo t m s t t p s
i p e r p( 8P a A t t i sr a t s yg l j a t p
o t p hr i
T r eo t o x a z2 w t d i m2 d n p p e
a g b t [ + 2 a t [ + 6 a d( 1I a 3 1 I w n p t s
t r o sd i f fb et t p or ea w h n b a t p c
o t t c y cs uf X a nD a to p s c o t a
A n r t p s e u9
d ua v s ma mo c ro a np rs eo X a s t p
t h a i n tt ro ~d s t3 ( F 1 f a O r e.
T o x yd iw n f ob p ao t a s oo t o x2 b i w
f oi 1 y ib i n t ei n ta s a o a t a r t s o t
o x a z2 T s t i i f o w a s a o o i w a l
e xo t o x a zt ht m eo i f oh n b e l1 N o
t o x yd i3 s 1 s ia st p s uw i s s q c
b s iT s t f r oo t p g i t s ym i r
12 +
&\ —
t2 2
h\N- ‘
\
t3
-
l+P
\
2 0\O
t P3
*
P
t -\
~
P
*
\
, -
t2
I- H
+
\
- N\ .N/
t3
h\\ : ‘s
t 3 P
X N o C 3
Y= C o N
W t d i t h1 a t d i m2 w h u r i t a a
( 6w i s ob i s pw n c ow a s c ya s a d
s er e a rI s ha o tt p ro g h a o t a p
t o t m o la t t m eg a o a s c a T s o t p w
e s ta t b rd i t4 b s c rX a ( F 2 f a O r
t a tT f o ro 4 i b r a tb a sr eo t p [ + 6 c
9 H K e a
c l o3 O wt t a bo a g l es u3 w u C b c t
f a r e s o n ab ei n t3 w r ea t 4 as g t f
p r4
%
1a
10
C
c“ JF 2 O v o t m e4
r M
0
F 1 O Rv o t o x yd 3
1 P
3
P‘N 0-
/I +
Ph S Ph
4L
3
o
*
s— / P
\
P
4
R 2 C—
4 4
-1
4 4
4 4
A s ir e a ro t p l[ + 6 c yi nw o w t r
t o t g e nu n rm et r i p h4 w t d i2 T
A n p s e u9
c o md n r w t a r n9 T r ew t d i2 o s
g ia r er ef n d i t oT o p w w i w t d
d r o t h i o4 T s ta si b m o s d w s
t p ro a a g rt p ro t m g o a s c a a t a o
h y da to t t h ir T p r4 s b f b t C b c o t
[ + 6 c y c4 a p rm iS ha o p rr a r b A et
a o s ii s o ma pI T i n df t s m t h
4 r ew n i t4 t g d i h y d r o4 v t [ 2 c 4
M o l( MC o n s
A s hi t T aw t e xo 6 c oo t f 1 a 2 a 4
H c o eo t a m i9 P Mc a ls t t r c o b
t m e sc o ma f ih s u fl L a H c oI c
t N La N c o eo 2 a 4 ( 5o m ec a v s
( 0 .a 0 . 0r e s pI t m s c oo t t h4 t p
o t 2 -s u bi s et wf t p o t m er ( 8 A 1 5 a
p r oa po f it t r ec eH of o t t a t 3 h o a
s me fo t c o ev at 2 c oi r f 0 t 0 b t c
o o tp o sw l t 0
T aM E na C o eo F ua M eC (
c 9 2
-H
p 3c
H c - 0 0 0,28 0.50 0.13 0.24 0.48 0.18
c 2 2 4
L - - - -H - - - - -
p 2 5c
H c
“ c c g
W t e x co t a m i9 t s o c oa t r c a s t
b [ + 2 a [ + 6 c y cc p ri a c ow i ro w t r
t ia H O M O (f ho H O M Om c W t
a m i n9 b t o c y cc p rc oi t r i H O
L U M Oc o nb o [ + 6 c y cc t p c oi t r i
H O M O ( f i lc o nT c o nw s t t c
g e no ci a H O M O (f hc om H w a f e
9 H K e a
t L U Me ng o t r eg es s s v f H
( f i d v e nc o nr eA de xc n b p f o
s y mc o n sw t a ma a c e9 a 1 i ng p sa
f [ + 6 c y cw d i m2 g b [ + 2 a [ + 6 c y
T r ep r ea s t d eo t s to m c a f
n q uv e rr e as hu w r t c ~ cp e rr ea e
i r e aT hs ta s t w s us uf ir o t t w p
v a n g es r t m d ec oc oh ew a i sw
a z uI b ua r er eo r es uc b i no t 2 o t
f ir it hr e as ha fa v ao p s ed eT c oo s
m e mh e tp ra h a a n oi t t r a 3 + 3 ~ 6 t w
o c l eo d i p or H e rh ew r s l t f h b g
a f of m e sc oe ib c lo d ir o b e o u ~ i
s t r1 f c y c l
E X PS
M ep ow d e to a Y ah s a a n c oI ( d s
t w m eo a H i3 o a J D ia U o a S U s
p h oN S pw r em w a J J N( M s o
s o li d e u t e( t e ti ns tN 2 a a f I
s pw m eo a J L A( M s p eM s ( w m w
a S h iG CO s p eX s c a w p o a R
A Fd i t lw g rm o nM K r aa a 1 r a g
E l ea nw p ew a P e rM 2 C hs w
p e ro M eK i6 ( co M K i6 P ( Y p m
d p rl ic h r ow u f p rl c hA s w
p u ra d rb u m ea t r ew m ec ow p u a
i na t mY ia b o i sp rw s up
2 - t e rd i m e t( N N - D i ms p
p af d i m e t( m 0 m w a t a s a c s o s f
b u t y l c yp rf 2 - @ r / -( g 0 m i t e
( T( m A f2 h a r t e mt m iw f id w w a e
w d i c h lT e xw w w b d ( Nc oa t r
w t r iw c y ca t s w s eo w d i( p 1 1 “
1 : 1 E -o t a m i9 ( 3 m 4 “ ( 4 ‘
I N e s st s a t r ev a
6 - A c e t o x( 1 E f o( m 0 m w a t a c a
A n r t p s e u9
s ts u so s ot e r l - bp rf t e r t( 1 g 0
m os oh y( m oT ( m A h t m u r h t
m iw c ot – “ a a s oo a c h( m 0 m i T ( m w a
A f3 h r t e mt m iw s oc od w w a e w
d i c h iT h ew ms u cw a s h c a b d
a c o n cT s w f oo c ow r ef h t g t a
v 1 ( 8g 4 5a y en em 6 “ I 1 1 ( 1 1 8 c [ N
6 1( s t -2 ( s M 6 ( m H 6 ( d J 5 H H 6 ( I d
= 5 1 H H -7 ( b H I 6 ( M 2 ( 1 3 ( 1 1 (
1 2( 1 3( C 1 ( 1 ( C 1 ( C 1 ( C M m ( i 1 (
M 1 ( M C H1 ( M - t 1 ( ( A C F C C 7 H
8 . 3F oC 7 4H 8 .
6 - t e r t - B u t y l -( F t A 9 A s o
t s y1 ( g 5 m a t a m i9 ( g 5 m i x ( m w h u
d r ef 2 h T r em iw c o nt rw m a t s w r
c r y sf m et g t c y c l1 a y n ( g 3 I m 1 “
U A ( E( c 2 ( 42 ( 42 ( 2 ( 2 ( 3 ( 3 n
( 3I 1 51 1 1 7 c I N 6 ( s G 6 ( s H 7
( m P 8 ( d . 1 H H 8 ( d . 1 H l N 8 ( & 3 (
& B1 0a 1 ( C 7 1 ( C 1 ( C 1 ( C 1 ( P 1 (
P 1 3( P 1 ( C 1 ( P 1 ( C M m ( i 2 ( M 2 ( M
– M 7 ( P A rC aF C 1C 8 . H 7 N 1 1 F C 8 1 H 7 N
I I . A s
F t a c e t1 A s oo t s 1 ( 1 g 1 m a t a
1 ( 1g 1 m mi t o( m w r ef 2 h S w g t c y
i 1 ( 1g 4 7
6 - t e t i - B u ~ l - l ,( P t A 9 A s
o t d i t h1 ( g 3 m a t a m9 ( g S m i t ( m w
r e ff 1 h T m iw c o na t r w s o a s c
( b et g t c y c l o1 ( g 5 r p ( m m 1 “
U A ( C( e 2 ( 42 ( 42 ( 3 ( 3 ( 4 n ( I 1
1 51 31 27 c I N 8 ( s 6 6 ( d . 1 H H 6 ( d . 1
H H -7 . 3( O m P 8 ( b s H l N 6 r 3 ( & 1 a
1 1( C 7 1 ( C 1 21 1 1 1 1 1 1 [ 1 1
1 41 6( C -M m ( i 3 ( M 3 ( M - M 3 1 M - C 2 ( 1 M -
C 41 ( P h6 ( t -5 ( & A C F C C 8 H 6 F
C 8 4H 6 .
F t a c e t1 A s oo t d i t1 ( g 2 m a t a
v 1 ( 0g 2 m i t o( m w r ef 6 h S w g t c
9 H K e a
t a t h1 ( g 2 9
6 - t e t i - B u t y l - l( A s o N - b
a n1 9( 2g 7 m mt a m i9 ( g 5 m a t p ( g 1
m mi t o( m w r ef 5 h T p rw s eo a s c (
t g t c y c l o2 ( g 1 r n e( m em 1 “ U A (
( e 2 ( 42 ( 42 ( 22 ( 43 ( 4 n ( I 1 1 1 1
8 5c mI N 6 ( 6 ( I d . 1 H 6 ( b s H 7 ( b s
H -7 . 3( m P 7 .( m P 1 N 8 ( & 3 ( f 1 a
1 0( C 7 1 0( C 1 21 21 1 1 1 1 1 a 1 ( C 3
1 6( C -M m ( i ) 3 ( M 3 ( M - M 1 ( 7 ( P 7 ( 5 ( &
B 4 ( 1 C 3, C aF C 2C 8 H 6 F C 8 H 6
R eo 4 - p h e n y l -2 w t 6 - (9 A
s o lo t o x a t h2 ( g 1 m a t a m9 ( g 1 m i b
( 1 w s to va r t e mA e vo c d w o d t
i nI h o t r e aS e po t m ib p rL ( g e l /7
3 a r e c r yf m eg 6 - t e r f -l ,( ( . g
a 6 - i el - p h e n, 2 ]( ( 1 g 3 .T [ c2 v n
( fm e tm 6 ‘ U A ( C( 2 ( 2 ( 2 ( 3 ( 3
n ( . 6I 1 51 1 1 8 c I N 6 ( s f ) 6 ( I d . = 1 H H
6 ( 1H d . = 1 H H 7 .( P 7 ( I s H 1 N 8 I 3 (
I -1 0a 1 1( C 7 1 I ( C 1] ( C 1 ( P 1 ( P 1 ( P
1 3( P 1 4( C 1 I ( C 1 C M m z ( i ) 2 ( M 2 ( 2
( 1M - M 2 ( M - - C H1 ( P 1 ( 7 ( P 5 ( t 5 (
A C aF C , 7C 7 6H 6 N 5 F C 7 H 6 N 5 1 T [
i s2 b lv in e( m em 6 ‘ U A ( ( 2
( 43 ( 43 ( 35 n ( 3I 1 1 1 37 c I N 8 ( s I
B 6 ( d . 3 H H 7 ( d . 3 H H 7 .( m P 7 ( s H
NMR 830.8( 3 1 ( C 1 ( C 1 ( C 1 ( p 1
( P 1 2( P 1 ( C -1 ( C 1 ( P 1 ( C 1 ( C M m z
( ri ) 2 ( M 2 ( 2 ( M - M 1 ( P 7 ( P H C 2
F o2 I 0A rC aF C 1C 7 H 6 N 5 F C 7 H 6 N
4 . %
6 - t e t i - B u t y l - 4 - i s[ c( A
1 ( g 2 m a t d i m2 ( g 2 m i t ( 1 m w r
f 1 d w ii ng b lU ns y1 ( g 1 w f o a a o h
a a t f iw s eo a s ic ( ha 1 : 1) t g t c
c l o p e n3 ( g b o c o1 y n ( h m 1
I 1 ‘ L ~ ,( C( e 2 ( 1 2 ( 1 2 n ( I 1 1 1
A n r t p s e u9
c mI N 6 1( s t -2 ( s M 2 ( s M 6 ( s H 7 ( t ~ 7
H P 7 ( t ~ 7 H P 7 ( m P 7 ( s H 1 C ( M 2 (
M 2 I -3 ( t -1 ( C 1 ( 1 ( 1 ( 1 ( 1 ( 1
( 1 3( 1 4( 1 ( C 1 ( C M m ( i 2 ( M 2 ( M - M
2 ( M7 ( P A rC aF C 1C 8 H 7 N 1 O F C 8 H
8 .N 1 1 6W t r ew p eu n ie sw t r t w
s h ot p ro v aa mo t 2 a , 4d e2 w s b N
H o wi c on b i sp d t d e hd a o p u‘ N o
t t e t r a h y d2 6 ( s t 1 ( s M 3 ( d J 7 1 3
H 3 .( b t J 1 H 4 ( d J 7 9 H 6 ( s H 6 ( P
6 - t e t i - B u ~ l - 4 - i[ c( A s o t
m e so x a t h2 ( g 1 m a t d i m2 ( . g 1 m i t
( m w s tf 3 d a r t e mT m iw c ho a s c
t g t p r3 ( g n e( e tm 1 “ U ~ ( ( e
2 ( 42 ( 42 n ( 4I 1 1 1 1 7 c I N 6 ( s t
1 ( s M 2 ( s M 6 ( s H 7 ( s P 1 C N( M 2 ( M
2 f -3 6 1 1 ( 1 ( 1 ( 1 ( 1 ( 1 1
( 1 4( 1 5( C 1 ( C -M m ( i 2 ( M 2 ( M - M 2 M
– 2 M2 ( M – 3 A rC aF C 1C 7 H 7 1 N F C 7 H
7 ,N Q . Q
R eb et M eO x a z2 a t D i2 A s o
t m e so x a z o2 0( g 2 m a t d i2 ( g 2 m i
t o( m w r ef 5 h S eo t p ro a s ic ( b
m e t1 : 1) g t [ + 2 c y c3 ( m 1 a t [ + 6 a 3 ( 1 g 1
W t p rw r e c rv s lf a l a o e a a v s a o
t o x yd i3 s eo 5 - r e r l1 ,l ,
1 , 4 - e p op y rI Lo t c o r7 - t e rd (
n e( fe ta cm 2 3‘ I 1 ( 1 1 1 1 c I N 6
0 ( s & B1 ( s M 1 ( s M 4 a 4 ( I d J 8 H H 7 6
( s H -6 . 9( m P 8 .( m P 1 N 6 M 2 ( M 3 (
& B3 ( / -5 a 6 ( C 7 8 a 9 ( C 4 1 1 1 1 1
1 31 31 31 31 31 ( C 1 ( C M m ( i 4 ( M 3 (
2 1 ( P h1 ( P h7 ( P A C F C 3C 8 H 6 N
2 ,F oC 8 3H 6 N 3 ,7 - t- d i- t ra
1 , 4 - e p o x y c y co t c o r[ c ]- i ( n
( fm e tm 1 ‘ I 1 ( C1 1 7 c I N 6 ( s 1 1
( s M 1 ( s M 4 ( t . 1 H H 5 a 6 ( I t . 1 H H 8
6 . 6( m N -6 .( m P 7 .( m P 7 ( m P 7
( m P 1 C N M( M 2 M 2 t 3 ( t 4 ( C 5 ( C
9 H a
8 8 a 9 ( C 4 1 a 1 ( C 8 1 1 1 1 1 1 1
1 21 21 31 31 31 51 ( C 1 ( C M n ( i 4 ( M 3
( M - P - M 3 ( 2 1 ( P h1 ( P 7 ( P A C F
C ~ 3C 8 3H 6 N 2 .F C 8 H 6 N 3 1
l , 3 , 4 , 6 , 7 , 9 - H e x a p1 . 1 3( A
s o lo t o x a z2 ( g i d et ( m w h u r f 5 h u
a rD ut r et b ao a ( m e w i ni nt t a a
t ha s yT s ow c o na t r w r ef e a t
g t o x yd 3 ( m 9 .p ( e a cm 2 ‘ I 1 (
1 41 41 3c I H N M( P 1 C N( C C 1 ( C C
3 1 21 21 21 21 21 1 1 1 1 1 1 1 1 1
1 31 6( C q u al N ( Q p m 8 1 1 1 1
1 6E l( e m ( i 3 ( 2 3 ( 2 + O - C 1 ( p 1 (
P h7 ( 3C Im ( i 5 ( M + H - P h3 ( 2 + 0 + H 3 ( 2 H
1 ( P h+ H 1 ( P h+ H 1 ( P F m 6 ( H A C
F C 4 2C 7 8H 4 N 4 .F C 7 1 H 4 N 4 S n 1 f a
s uo X -a nd
6 - t e1 l - d i m e t h y l -1 u n1 (
A s oo t m ed i p h e1 ( g 2 m a t d i2 ( g 2
m mi t o( m w r ef 5 d T m iw c ot r w t w
b e na t s ow c ot g t p r4 ( g 6 p ( e a m
2 ‘ I 1 ( C1 1 1 6 c I N 6 ( s M 1 ( s 1 1
( s M 3 a 3 ( I d < 2 1 H H 5 ( t J 1 H H 7 (
m P 7 . 7( m P l N 6 ( M 2 ( M 2 ( t 3 ( t 3 (
C -4 C 1 7 C 7 C 1 ( C 1 1 1 1 1 1
1 31 31 5( C 1 ( C M m ( i 4 ( 3 ( M - S 3 ( M -
S – M 3 ( M – S – M – [ A C F C 2C 7 H 6 F C
7 4H 6 .S n 1 f a s uo X a nd
( 6 - t e t i - B u & l - 4 , 4 -[ c ] t(
A s oo t t h i a z4 ( g 6 m a t d i m2 ( . g 1 m i t
e ( m w r ef 9 d T m iw s eo a s ic ( t g t
p r4 ( 0g 1 r eo rp ( m em 1 ‘ U i ( (
e 2 ( 42 ( 43 n ( 4I 3 ( 1 ( 1 1 7 6 c I N 8
1 ( s I -1 ( s M 1 ( s M 5 a 6 ( I d J 1 H H 7 7
7 ( 1 P 8 ( b s N 1 C N( M 2 ( M 2 ( t 3 ( t
3 ( C -7 ( C 1 a 1 ( C 7 1 1 1 1 1 1 1
1 31 31 31 31 41 41 ( C 1 ( C M m z ( i 4 ( M 4
( 1M - S 4 ( M - 1 -3 ( M - P - P h3 ( M - 2 3 ( P - t
B 1 ( P hA C aF C 3 3C 8 H 6 N 2 F C 8 H 6
A n r t p s e u9
N 2 , 6
W a i nt M H i[ M A A a M R A f e a
t aT w w s ub a G r af S cR ( 0 a 0
f t M io E d uS cC ua S pJ
1
2
3
4
5
6
7
8
9
R EA N
H e t eb c y c lP 1 P 1 K oT M H K H
H e t e1 - 3 1
P ar ei a p r ef K H K oT C M l H
A kA K aA ( ’( ’1 1 0
R eo c y c lr eo m ec oP K T M R
S yh 1 , 3( . j w( ’P A E W N Y V 2
1 9p 1 -
R eo m e sc oi nc y cO M K H S
a O tM e sC o mI N c j tA ! .S J P E A
N Y o1 9p 1I7 –R aC A M eH eI ( ‘ o
o r( ’ hB aD H R O W D E P eO V 4 1 p
1 7 1O lW D R aC A M eH eI A H
( ‘ hK a tA R B oA J E A cN Y V 1 1 p 1
1 N eC G R aC A l k t1 3 2 9O W D S
f oS P T e f1 4 2 2G iH L B J S M O
z oI T ( T ho H e t( ’T I D E W N Y
4 1 9p 7 3
M a tH K H . ( ’, ( C a1 4 N S
H i rK K iT K H . ( S ( [ “1 6 I
M a tH K H . ( ’. P 7 i1 1 6 M H
K oM K aH C hL e1 1 1 K H N aS K
T H i rK . ( ’S P e7 r1 1 6 7K oT M
H K aH H e t e1 4 31 1 ( A E T S V 7
h e1 94 0 2P oK T B J H oE . O ( 1 4
8 1
M a tH K H . ( “S P T 1 1 2 5K H
K o bT H oK O gK M oM J ( S P T f 1
1 0 5
K aH T oS . ( ’S ( ’C o1 5 1K H A Y
H a sM M aM J ( ’S ( C o1 9
K aH T oS A rY M aM H aM I K W S
M i yA . ( ’. SP eT I 1 2 0
K aH K o bT T oT S hS . ( S P T 1 1
9 H a
10.
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
1 7 –
K aH A N K aY Y oK . ( S P T 1 1
1 2 4C a F r iW S cW L A ( 1 4
4 F r i eW S cW D e bT L A ( 1
4 9D e b aT S cW F rW L A ( 1
5 0
R eo s ya p ro p s eT H P sI
A aH e t( ’K aA R E A cN Y V 3 1 p
1 8
A bJ R H D J A ( ’, 1 f 6 8R i r h a 6
t e r / - b u t y l
H aK V oK H P lG K C o , $1 C V 5
H aK S cG W aK L iA ( 1 6 3
T hr ew c a lw p ro b “ PM Ow i b
o t M O( 6 Q N 4 o T S C
( ‘ r }d f t o x yd 3 C 4~ = 4 M o~ a
= 1 2 0b = 1 8 .c = 1 7. V = 6 ~ T = 2 K D = 1 g
c mF ’= 2 R = 0 ,R = 0 G = 1 f 1 d [ 3 c
A tc o ob l ea a na t p aw b d a t
C a mC r y sD C e
( ’d f t d i t4 C 2M = 4 M oP a =
1 5 .b = 9 ,c 1 6& ~ = 9 5V 2 2~ T 2 K D
= 1 .g c F (= 9 R = 0 R = 0 G = 2 f 3 d [ 3
~ (A tc o ob l ea a a t p ah b d
p oa t C aC r y sD C A r t t C f t
m as hq t f l ic i( 1 a t r en 1
A vM B aR C a bA C iP H F J J iJ L P J
C . o C h1 6 3 7
L eT , C S 1 3 2
T hC J V oD J o S j1 C V 5 9
G o tH W e iM C C hB ( J 1 1 7
H a dM J K aA M F rJ P J O ( 1 4 7
G o tH ( ’B 1 1 1 8
C lT J N T A S y1 5 8( S K J L R D , O
( ’1 94 1 8 4
O hM C hH S C I cK N K Z 1 8 4
( (A b1 6 1 4P K T H oE S U P J o (
1 93 3 61
( R e6 N o1 a c1 M 1