J. Org. Chem., 1998, 63(6), , DOI: /jo972154b

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1 J. Org. Chem., 1998, 63(6), , DOI: /jo972154b Terms & Conditions Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machinereadable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at Copyright 1998 American Chemical Society

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3 00 C C000 - UCD L WO - 0) 0 * 0r- La CN =0 - d) ") CN C:) 1-0) cn 10 - CO - -D C :N N - C CO0 ID L 03.0 C) L CO I * ro O) l N - n orf C C C O "rw N CM clq " ~~ ~ ri~iip~ IIIjhiIp~,uI~i itji.irp i.ir~iirnjir * I' ppm /giga/data/qtian/nmr/ctian.406.fid/1/pdata/1 unknown Mon Aug 14 00:20:

4 so co -o r Mo -.0 In C c , l c.d' CD Q- CO d- -o- CO -4 ) t ) CO l "I "- 04 C1 C j C N. '.J. '.J CN0, co r, CC O "11c CO CO Inr M.0 00 CO.3 W O COCCO IO') - j~j~j ~ I i J T-Bu r~o~1 j~2~ Z C) U C C4 f~~00, LC l i. I I.... -T-r-r I I. I. I. I. I I. s I f I I I I.. I I -r-t-t-t-1 I I ppm /giga/data/qtian/nmr/htian.649.fid/1/pdata/1 unknown Fri Mar 8 16:29:

5 CG =o C> co - N 11) m~.lc ~ ' C C ( fl~ C to 10 Lfl C14 C)~-~ tfl ~ f ~ ( L N( OD tl - Co -L W.CC- Col to fl (NI t-bu ppm file:/giga/data/qtian/nmr/ctian.308.fid/1/pdata/1/plotfile.61 user:unknown date:fri Jun 23 21:27:

6 CO - fl %r) m as 03 ar LI) CO ).) 0 m- W CO.- CI 0 Cc C C!O ( o C. a I - - CO 0303*-W0W0D03 r- r- - r cy c- r- r- Ko Ko LI._K.o K CN - a -e.-. cd c-0 tx om cd m o L IN CN ccm c 3o0 co co Lo o LD LD I -I- -~ F -f f/, I I.. I. i i F7-r-= ppm /giga/data/qtian/nmr/htian.644.fid/1/pdata/1 unknown Tue Mar 5 20:12:

7 to,-~ -~ tr~ ~ r- 0 a~ '-, r~,') ~ ~* r- ~ tor- to to r- C,fl ~ to -~ m0-0~ to r- to I CD C> -. '0 ' I I ppm file:/giga/data/qtian/nmr/ctian.283.fid/1/pdata/1/plotfile.1 2 user:unknown date:sat Jun 10 22:30:

8 1N 04 MJ M~.0 LO. JO CC. ) I j 47,j (Nj I= a, a) JLo td -~ 03 a l-- U- j) ( ) mo n Jh CO I-) 1) C -P-- - ~ O -O - -O - -N - -n V mj~ m l - N -Ix- 'I,l 1o- a-fl~~~ ' N -4N a-l0' N (J( -r -, - j -I /giga/data/qtian/nmr/htian.381.fid/1/pdata/1 unknown Wed Jul 26 09:40: ppm

9 C=3 m0 1")m o 00 1) 10C 1 1 m~a o 1- - r) un CO C coflo 1)cN- CN i-i r,4 CN Il I rir' lt w" Ohio i 10." " I " ". I ".". I... "..I'". " I " " I ".."...I' "..."." I. ". I. ".. I.. I ",. I " '.... Ii." j.i ', I j r. -e1-1 1 i t PPM /giga/data/qtian/nmr/ctian.404.fid/1/pdata/1 unknown Sun Aug 13 00:29:

10 r co n n en Ca CO rf) Ltr rn cn c" e) m Lo TO 010s r--r- or- r -In In c- ( r) (11(N q n ) (N (N (N NNNC1 i - in D C CD c0 m 'n In - N (N *-*. - - en 0e CO 4 tin. e Cr mo w to- ID Ln - ') -. o....a eo co -D r) n e. CO cno O) n rn ( r... In In (n 1) -) ) 1) - 1) -,1) r ' 1 04 (N (N 4 (N -N -N -N -N - (N L LJXj~L j _j I -f I/ lfr 1 1 -, a' 01 a'k n : _ /giga/data/qtian/nmr/htian.394.fid/1/pdata/1 I i I sir-tt ppm unknown Thu Aug 10 13:45:

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12 ) m c o) In m.- In W) In ) co "mm 1) m 1) 0 el - - S- 0 C) cc ca m In er o lo C) Cn - - C3 c c) m c~ C) d- -r. -. r- r. - ' - -r.r--- r- r- r co.l t II*~. - CD N N - - C) 0)C-om C) - "I - " " I) - 0 " C W.o Ono M m N C>)))CCCc M N >c N C)C L O ED 0 )....I.. 1 f f f ii C) C) *~) C) C) C) 0~ 0) 0) 0) - C) - (N. f2 71 h ~NjNj r C= CD C /giga/data/qtian/nmr/htian.659.fid/1/pdata/1 unknown Wed Mar 20 09:27: ppm

13 .- 0 *- 01 r-- C a, (1o Da O. ro 03 as 11 o r-c CC O n D. - -mn c CO [ 0 on r 1) In 1 " CN CN bb N IPn SiEt ppm /giga/data/qtian/nmr/ctian.660.fid/1/pdata/1 unknown Wed Mar 20 15:25:

14 '~ CO'. - M WO W. MO MO W. l r '.0 '0- ~ CO~~ ~~ CO- CO -) -1 In- In In -r - -r D L0 10 c'jc: 00C 'n In )M O CDm CD.1 11 f ~ i -f Jf/ ppm /giga/data/qtian/nimr/htian.390.fid/1/pdata/1 unknown Mon Aug 7 21:17:

15 Ln w) - l - c)c N C) m N -, -n I -O -f -~ -f - - C- -t -) I-~ "N " r-) c:, 0, 'n~ cc cn LO I~ n In' IN "N' 'N V 1~ I~i M li. WOO#~ II-- I 0 rrrrrprnr ppm /giga/data/qtian/nmr/ctian.405.fid/1/pdata/1 unknown Sun Aug 13 07:56: YtdTWWrVW*WflflhIVVWr,, rwv I wyrr,'n~,.-,rrn-, Y~ VT~qrW j.~.,. n.vr.--..

16 1) co -* *Uo *r) -~ * ) 'C) -~C C - r- ~ ~ ~ ~ I 1) In 11) In r- r - r N - - r- r- r- C "C) C) 0103 m r ID LoI -"c m ) 0 - h- ~ Nc) Lo0 m~ f- 1)n -f m30 w- o n s t- r- r- Lo300 o f a f o.f) Lr Jn n) o Cr N - -N m o (.0 0Lo3.~. ~.. 1. / Ii. I I I1/ -r-~r 1-303r--TT--T -- T-rT--r -T 'l " " I " " ' " ll ll ljar l 'I.n Iaja ril - " l" 'l" " ' ~ ~~r~i ' ~.. I i...rr l' ppm /giga/data/qtian/nmr/htian.366.fid/1/pdata/1 unknown Thu Jul 20 21:33:

17 al XJr - (I )'"( 1( O~ - Wf a- I I C ( C) ~ r - -~ -~ -~ - N - N - N N (- -- A~L~i1 WOWNW, ' 4% W ak I.- II.iIWI,,I....I,,1. l.,1. 1f l 1 ' '..I ~ -- F -r - - I ppm /giga/data/qtian/nmr/ctian/381/pdata/1 unknown Fri Jul 28 08:48:

18 a, c r. n -. - a - In p z) 0 co c a- " n.- co to rd r at a --. '0 C o, M0 Wo 00 r t.0 (o to no a 1) an -4 N - CD c c 00 Do co co r r- r Sr-- r- r r - r-- - r -- r--- rt -- r-c o o o a o to A to I i l I I I I I 1 n cc) " ocomeo r (N coa v 0 M a" a 0 o o r, r r o 0o0o me - ( c ND n 0n ro r - mo00o r) v ej e r- o.-- r. a )n ao) LO r ar an) r- ao r n Co n ana a nn -- d- - - v----c) coo (D CN (D C000 >0000 >co 00 a r) a) a) r) r) 'I 1-) r -) a-) r -) re ) t to - (N (N cy (N en (N (N (N cn cy ev ( e ( cy (N (N ~~i~ jii ~ J iill r c0 or r- r" a-) r - - o c co I Liv I It I n I I I e I Is Ia V-I1 I I, II I I I I. 7 I I I I I I I I I I s i s e s I I I C)~ I cn /giga/data/qtian/nmr/htian.803.fid/1/pdata/1 unknown Wed Jul 17 20:38: IPP ppm

19 n en co m r. (o r-. a C) c oc " c( 0- (.0 a I -r (fl S- en rl.0 r- W.0 - c=m mo r) c on 03 'o a f ') I- " "N 'N I.N..N D to 'N 1) 1- ) cy - -L 10 ' mo rn -03,n~ -0LO r r- le I ( co (.0 OH ~JA I I I.' I '. I I I ' I I 1 i ppm /giga/data/qtian/nmr/ctian.585.fid/1/pdata/1 unknown Sun Jan 21 21:23:

20 I " c, to C:) " 00 C C a C *D Lo a n LO LO 4l Ln V) F-- (N 0 ar a'. CO P ' 0 CO " CO L L Ii C) CO C F ) C )C m In PM unknown Sun Jul 21 09:05: /giga/data/qtian/nmr/htian.808.fid/l/pdata/1

21 c)c c)v oo-, cr'-~ m m ~ -~~ col rl, o - c c I) In r-n 1) n 1) 3 a..~~.,.- r..~.n n r- -O I I I t I6 W 11 -m' m'''' li ' l I ppm /giga/data/qtian/nmr/tian012/1/pdaca/1l unknown Sat Sep 30 01:12:

22 N r) 01 - p. wo LC) m m1 CO - wo LO r1 01n "I.D mo - c.n (f "- (N - o' Co (tl) c &I.ln c) Ln P- 01 C C) r1. &I P4,' 0m La0 (0 co0 ( ,.o L.o P. Lo -~ - " - 03, m1 m. mo DO (l Lm ) (N P. ) ".,~ m-0 n rn n ) n(~ r- P-. r- F--.tl 1),. -- Ln Ln C) (C) C) C) &) (n N N "N "N N "N N (N.N.N. -. O. O.oD P... F... P...N.N.'. P...-.N.N. N.N.N.N (N... N. (N (N. CO. m nm r,rr,r t r liii r r r r r,,r r,r- o DL f II ) / i""l""i""i""i" I j 0 )L1 Lo H '1 I T P CO - C - I' l /giga/data/qtian/nmr/htian.811.fid/1/pdata/1 unknown Tue Jul 23 21:00: Ii ppm

23 00 Mm co~n GO (N GO ) 0' D ~m ~~ ko - m WO c' ) wo m) O Lnc =- O n r r, to0,n m' m' mo 0 r-- LD w. (. -) - - (Nc.. GO ~ ~ L (.0 -,"T In 'T) -n r) ") "~ (N.N.N.N c4 (N ( NN - N(-N El ppm /giga/data/qtian/nmr/ctian.821.fid/1/pdata/1 unknown Tue Jul 30 08:21:

24 - r. " o m in c01o i o. v co i. - -4O 'n 0 'n t- o Cr or - r- in C r - ) - o N co. cc i r o - C oc Mo0 a, IN to n. - r) ) ry - C cn co =co- toi n In I In " - - C3 C Cm00 o o L c C i, o CI rr - - I IN i- In- 10- r - I ) IN 1) - n In r- In I- "N N 04 " i-. "- I N. N r- NI N I4 -N -N I- -N -N - -N CIN "011. Cn In 11 In..I. IL~. L...JI I ] i..i o> C) ev - Ocoto C) in 10 CN 0 \0o / I r r ii -t J Li U 11II. I l ii ppm /giga/data/qtian/nmr/htian.822.fid/1/pdata/1 unknown Mon Jul 29 14:50:

25 ,n In LD 0 o (0 (0 =~ m -) c) C)n In ) Ln r) D I =0 c) In r r0c).ln - Inen cv -I o o In ) l n r) La 0) In I -0 m - el -C C, cd C 0000m0W0m0 r- to Ln )00 In n r) I) I) In In "N "N (N "N "N (N "N(4 co Lo Lo fln - n m~ In In) LO Inn In O0A O0v O h, ~ ~ ~ ~ ~ ~ I ~ ~LLI.L /giga/data/qtian/nmr/ctian.824.fid/1/pdata/ ppm unknown Mon Jul 29 22:18:

26 emalrn o me, r secocornomz) er - m oal t 3C Oe (71rmCemato ot o m mac D4 C1ci"n Moorm- - ecs.n--ca mmew rr csev.- - mmoon3ne cacor-n In3,'oLn<~ - - r- F- F -- r -r-- r r- a o o o o o to o to < C L o n a Go CO CO CO CO F- - r r- r- F- t - --, r P - r- - r- r-- T- f - r. S O Me CMe 3 11 CO 4 ) _D LO cd C C-.1 Cn /giga/data/qtian/nmr/htian.815.fid/1/pdata/1 unknown Wed Jul 24 10:12: ppm

27 r-. ~fl - Lfl (N CD..~- (N Cl) ~fl c:, Ct) c; - (N (N m) Cr) In C- lo r D.n) CD In) cc 0 D In - I - -)( D -. In),) C-) (N.N.N (N (N j c-4n( 0n (n -Ln t) cd LDr-U M In a, (N) C-) 0, CD 0~ CD ys le3 200 I 180 Ii I.111 ~IIt /giga/data/qtian/nmr/ctian.831.fid/1/pdata/ T r unknown Fri Aug 23 10:47: IA 20 0 ppm

28 03a %3 c C'. " o W - w ), oo a0 3.0 C) - fn m~ -) a, 00.0 'o- 03 m (N m, m L"" r-. m to - co W r-. 3.,LDL O C'J 3'I cc, " o 03 rfl '- (N o~~~~~~~~~..~.-.1 -~ ~ ' r.. r 3d-) I-- L Li.-- W Y -L-_J Lj - J I I.- ') f.1-i,,. C _ 'cn C, I I. :: CD C:, I. I I I - I I ppm /giga/data/qtian/nmr/htian.827.fid/1/pdata/1 unknown Tue Jul 30 11:00: r-i-j

29 Cm -) - 0 O0=) MO= (= D k -fl) O= - LD - 0 LI PO C D; CD 00 O 0 r - Ut r- LT cn 0 00 L r t 0 D co r a o> m, 0 00 o a C: 10 In C- 0 r)11 C, 10 r t -I. o> 0 O0 V o0 O Gges gel ~'c~.;.:i,':~ *A;7,.;; l.~....,.. i,~...:. ~,:;jt~'~ ~VM6~~ ~ ~ -~ ~ A J~L$k~J~44$AM 4J~ 4 eqjr ~ I II I I I I I I. II'I- II'I, li I I I.' I ' I ' I l '. I ' /giga/data/qtian/nmr/ctian.820.fid/1/pdata/1 unknown Mon Jul 29 22:46: I. 0 ppm

30 - o o' c m r C> a r- 'n.- r- ".o e. e- 4 " elr N a m r- m (N 'n (N co - - me c =-co - = (n - 3 C to <0 u n Ln to c> co r-- Ln te ad Wo <w uo Ln r es e ) ew u- a co ao mo an - o a e.. to ) 0 f- (1 P, I- T 40 D 4. LO L(N L f r) In fl N r- r n c- rd N N c 0 r - r--. r.. r- r- r - t r. r- f- r-. t. r- C t ( I-- - r I. -. it It I L LL...-LA L J -1 Jii ~/~ I Li r1i CN ppm /giga/data/qtian/nmr/htian.709.fid/1/pdata/1 unknown Mon May 13 21:05:

31 C - rn 0-13 In - C)0 r M- 0 - r r - In Cc n rn CO I Lo CL c N. CD 0) ro) r 0 ca Ln ad 0 ('4.- co W om Co o c Co - o> - Co c00 l- m r0 or Co r) ev co (Dca.- -- W000 r--r- ' -0c o00n o r- en r"- rn-00 r o. o o u r. r- 0 I II JL % A~J- J O t or11 > I- *i -rw S I ' I I - I I ' I I 120 /giga/data/qtian/nmr/ctian.709.fid/1/pdata/1 1I " unknown L~J.. -.~r~jj ~0~j ~ trvrlrr.r.,qn "WWNWflYflflhI~fl~Uflfl~~ I I ppm Mon May 13 22:21:

32 Ln i - r- [ r- f- [ r- I ( - IW T-n m- r m M l "'n i F r-- m F 0- F-- 14 I I I t LI II I I I L_ L CMe 3 f i-f- I ~I0T Lo IL (Nl r0- ifl ca "" l " I " '."... l I. I.. ' * I " " I '"".1 I'.. ". j " l. " " " " l " /giga/data/qtian/nmr/htian.686.fid/1/pdata/1 unknown Thu Apr 18 17:08: ppm

33 C~ o t to,-.r- Z~ -. r~cn mo r- r- fln toj r- Do r-r.-w0, rn 60f C )-C o I- - r- - e-, to n a) c. C) fl r- - r- to r- r r- r- to ~r) to 0, C; "' CN an LO LJ-) 0D r- J. CMe ppm /giga/data/qtian/nmr/ctian.685.fid/l/pdata/l unknown Sat Apr 20 06:32:

34 m 0 (N P as C) "r P- ) On CD m D OZ>N r (N C> - " C n4 In N Ia In ) n C 0Cn ) L VN ) Ln ) L LA 'r ( r r.rn 'r "w., ") f) n 1... p r r - - C- r-.-- C-- r r iij L t-a-, - C) 2 C CD CD CD C3 C) C) Th 9.0 Ii a, r - <0 C: CN <v -WT 'Hil oa C ' llhil Ht /giga/data/qtian/nmr/htian.830.fid/1/pdata/1 unknown Sun Aug 4 10:26: ~ ppm I

35 ~~~~~~n ~ ~ or-.f ~ I -,.- 3 c.o0o c". c'j m O ~ cn~ C m~ r- r-. r-- r-rn In- In r)' c. cn( N( N( CMe 3. 1 I ' I II I I I ' l ' " I' /giga/data/qtian/nmr/ctian.830.fid/l/pdata/l unknown Sun Aug 4 11:19: I T--T ppm

36 m00 0 in D 0 CO W0-0 o S LD.0 0*1- OD 0- m- I nc 0 0 r~ - r- r- r- r- r- r- r- r- r- 0l C:, 0 In " ~Me CMe 3 I V~L1 C> 0. CN C14 = q--r-,r-rj ' I l " l " ppm /giga/data/qtian/nmr/htian.727.fid/1/pdata/1 unknown Fri May 24 20:26:

37 ) 'a oa 10 -~ 0) tn '-p LD r) - n t) rn Ln C4 0 Cn n Q ' - A 'D C) W) - r On CD CN CN ". O" CN O C- -D a to rl) toc CO- In - In -l L I - I) Z) L+ -F 'N 4N 1 ( pn( 4 Me CMe , OAM j 1-1 I L I I.' I ', I. I j I I I ' I. I ', I I I I I I I ppm /giga/data/qtian/nmr/ctian.727.fid/1/pdata/1 unknown Fri May 24 21:54:

38 In -,-- Cm ) rj cy o r- LD Mm I- -O tlo C) r LO to C) (= rc to W CM r1 Cn cor-- Cn r) rj na Con r- CO C) r! C < - Co C o co 0 r r- Cn Cr r m mm C C o )C n or r ) r ) r ) r o 4 CD I SiMe 3 a] r- 4ne]r ~I.~ ~II' I I I* 1****[****1 S ppm /giga/data/qtian/nmr/htian.720.fid/1/pdata/1 unknown Tue May 21 15:45:

39 m - O C> I-) ID-oc )r = -C I 0 - C n N ~ SIMe O ppm /giga/data/qtian/nmr/ctian.753.fid/1/pdata/1 unknown Wed Jun 19 21:10:

40 O > r- =, - wf " c) wn 'n co to C) 0'' =' r- Co in. '0l C) rn Ln r- Jr-f l f 0 - C C) LoLoL Lo r -, r-d- - CN "- "- r i- r ~- > r C- C:) C)- m~ M~ m0 m0 co WO md M0 r, ' I ~ ~ IID ~ LLK)JJin~L~ ~ ~ II0 ~ LLLLK ~ 1 Ii II ~ 11F1I Lo I Me J -f -J L-i /giga/data/qtian/nmr/htian.791.fid/l/pdata/1 unknown Tue Jul 2 09:30: ppm

41 (Nrro f 0CAN c0 s )r-m In -0 NW m O =.- 03 co 0 n-0, N 0-4 * Lo r4 ) 0 0)0 O C) - 0 r 4 L L 4L) t N 0 (N N 40 - O - o a r o -o 0o )- (N 40) r) ca 0 r- Lo 4 (11 CD rlplr)rri{lto N Vrt C / \Me I I.. I - I l I I I I I I l I l' I I I I I I I /giga/data/qtian/nmr/ctian.790.fid/1/pdata/1 unknown Wed Jul 3 22:28: , I.1'.. I ' ' ' ' ppm

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