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

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J. Org. Chem., 1998, 63(6), 2002-2009, DOI:10.1021/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 http://pubs.acs.org/page/copyright/permissions.html Copyright 1998 American Chemical Society

o L.(- " -o m co'o --o. - o C) o D -* * co l O <D In Inshn 0 ~ y- - D O --- 1 1C C ~ -o oooc 0 F-) F-f).'~ c-j r.z.-~ '~) '-~) vi Ltnc Co. craomoco, cor r-- -f -) - 0-000 - f - 0 - --- - C- i If 9.0 8.0 7.0 6.0 5.0 4.0 /giga/data/qtian/nmr/htian.397.fid/1/pdata/1 3.0 2.0 1.0 unknovwn Thu Aug 10 19:22:45 1995 0.0 ppm

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 " -- - - - - - - - 4~~ ~ 140 130 ri~iip~ IIIjhiIp~,uI~i itji.irp i.ir~iirnjir * I' 120 110 100 90 80 70 60 50 40 30 20 10 ppm /giga/data/qtian/nmr/ctian.406.fid/1/pdata/1 unknown Mon Aug 14 00:20:07 1995

so co -o r Mo -.0 In 00 -. C c-. 00 0, l c.d' CD Q- CO d- -o- CO -4 ) t ) CO l "I "- 04 C1 C j C00 0 0 0...... N. '.J. '.J.. 0500 0 CN0, co r, CC O "11c CO 1 0 10 CO Inr M.0 00 CO.3 W -.00 0 1 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 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nmr/htian.649.fid/1/pdata/1 unknown Fri Mar 8 16:29:03 1996

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 180 160 140 120 100 80 60 40 20 0 ppm file:/giga/data/qtian/nmr/ctian.308.fid/1/pdata/1/plotfile.61 user:unknown date:fri Jun 23 21:27:02 1995

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.1 1 1 -F7-r-= 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nmr/htian.644.fid/1/pdata/1 unknown Tue Mar 5 20:12:15 1996

to,-~ -~ tr~ ~ r- 0 a~ '-, r~,') ~ ~* r- ~ tor- to to r- C,fl ~ to -~ m0-0~ to r- to I-....0 CD C> -. '0 ' I I 180 160 140 120 100 80 60 40 20 0 ppm file:/giga/data/qtian/nmr/ctian.283.fid/1/pdata/1/plotfile.1 2 user:unknown date:sat Jun 10 22:30:30 1995

1N 04 MJ M~.0 LO. JO CC. ) I j 47,j (Nj I= a, a) JLo td -~ 03 a l-- U- j) (010-. - 1 ) mo n Jh CO I-) 1) C -P-- - ~- - -0 -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 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 /giga/data/qtian/nmr/htian.381.fid/1/pdata/1 unknown Wed Jul 26 09:40:40 1995 ppm

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- 140 130 120 110 100 90 80 70 60 50 40 30 20 10 PPM /giga/data/qtian/nmr/ctian.404.fid/1/pdata/1 unknown Sun Aug 13 00:29:09 1995

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 : _ 9.0 8.0 7.0 6.0 5.0 4.0 /giga/data/qtian/nmr/htian.394.fid/1/pdata/1 I i I sir-tt 3.0 2.0 1.0 0.0-1.0 ppm unknown Thu Aug 10 13:45:27 1995

a - Cn -: (N Cl Cl 10 (0 C C r-~ r- r~ (0 r~r- r-. r-. LD WO Cm I'ED Lo; rn- c O - al CO m tr CO. C 4 tr 4 (N LO Ky) 190 180 170 160 150 140 LW 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm /giga/data/qtian/nmr/ctian/395/pdata/l unknown Thu Aug 10 22:59:32 1995

) 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 15 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 /giga/data/qtian/nmr/htian.659.fid/1/pdata/1 unknown Wed Mar 20 09:27:34 1996 0.0 ppm

.- 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 3 180 160 140 120 100 80 60 40 20 0 ppm /giga/data/qtian/nmr/ctian.660.fid/1/pdata/1 unknown Wed Mar 20 15:25:23 1996

'~ 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/ 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nimr/htian.390.fid/1/pdata/1 unknown Mon Aug 7 21:17:31 1995

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 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm /giga/data/qtian/nmr/ctian.405.fid/1/pdata/1 unknown Sun Aug 13 07:56:38 1995.YtdTWWrVW*WflflhIVVWr,, rwv I wyrr,'n~,.-,rrn-, Y~ VT~qrW j.~.,. n.vr.--..

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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. 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm /giga/data/qtian/nmr/ctian/381/pdata/1 unknown Fri Jul 28 08:48:27 1995

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-0000 4 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 - 0 0 n Co n ana a nn -- d- - - v----c) 000000 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 9.0 8.0 7.0 6.0 5.0 4.0 3.0 C)~ I cn 2.0 1.0 0.0 /giga/data/qtian/nmr/htian.803.fid/1/pdata/1 unknown Wed Jul 17 20:38:44 1996 IPP ppm

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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 01 01 La0 (0 co0 ( - 01 0,.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 0101.01010..-.. 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" 11.0 10.0 I j 0 )L1 Lo H '1 I T P CO - C - I' l 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 /giga/data/qtian/nmr/htian.811.fid/1/pdata/1 unknown Tue Jul 23 21:00:51 1996 Ii 1.0 0.0-1.0 ppm

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 180 160 140 120 100 80 60 40 20 0 ppm /giga/data/qtian/nmr/ctian.821.fid/1/pdata/1 unknown Tue Jul 30 08:21:35 1996

- 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 "-. 04. i-. "- I N. N r- NI N I4 -N -N I- -N -N - -N CIN 001.01 "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 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nmr/htian.822.fid/1/pdata/1 unknown Mon Jul 29 14:50:15 1996

,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, ~ ~ ~ ~ ~ ~ 140 180 160 140 I ~ ~LLI.L /giga/data/qtian/nmr/ctian.824.fid/1/pdata/1 120 100 80 60 40 20 0 ppm unknown Mon Jul 29 22:18:12 1996

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 - 0 4 O Me CMe 3 11 CO 4 ) _D LO cd C C-.1 Cn 9.0 8.0 7. 0 6.0 5.0 4.0 3.0 2.0 1.0 /giga/data/qtian/nmr/htian.815.fid/1/pdata/1 unknown Wed Jul 24 10:12:17 1996 0.0 ppm

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 ~IIt1 160 140 120 100 80 /giga/data/qtian/nmr/ctian.831.fid/1/pdata/1 60 40 1.. -- T ------ r unknown Fri Aug 23 10:47:11 1996 IA 20 0 ppm

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 -~ ~ - - -03'00. -.. 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 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nmr/htian.827.fid/1/pdata/1 unknown Tue Jul 30 11:00:38 1996 r-i-j-7......

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 '. 180 160 140 120 100 80 60 40 20 /giga/data/qtian/nmr/ctian.820.fid/1/pdata/1 unknown Mon Jul 29 22:46:51 1996 I. 0 ppm

- 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 - - -11-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 00 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nmr/htian.709.fid/1/pdata/1 unknown Mon May 13 21:05:14 1996

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 ' I8.180 160 I - I I ' 14 140 I I 120 /giga/data/qtian/nmr/ctian.709.fid/1/pdata/1 1I 100 80 1" unknown L~J.. -.~r~jj ~0~j ~ trvrlrr.r.,qn "WWNWflYflflhI~fl~Uflfl~~ I I 60 40 20 0 ppm Mon May 13 22:21:15 1996

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 " 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 /giga/data/qtian/nmr/htian.686.fid/1/pdata/1 unknown Thu Apr 18 17:08:22 1996 1.0 0.0 ppm

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 3 180 160 140 120 100 80 60 40 20 0 ppm /giga/data/qtian/nmr/ctian.685.fid/l/pdata/l unknown Sat Apr 20 06:32:19 1996

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 -4 0 0 '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 8.0 7.0 6.0 5.0 4.0 /giga/data/qtian/nmr/htian.830.fid/1/pdata/1 unknown Sun Aug 4 10:26:51 1996 00-~ 3.0 2.0 1.0 0.0 ppm I

~~~~~~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' 180 160 140 120 100 80 60 40 /giga/data/qtian/nmr/ctian.830.fid/l/pdata/l unknown Sun Aug 4 11:19:21 1996 I T--T- 20 0 ppm

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 " 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 0.0 ppm /giga/data/qtian/nmr/htian.727.fid/1/pdata/1 unknown Fri May 24 20:26:59 1996

) '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 - - 00 to rl) toc CO- In - In -l L I - I) Z) L+ -F 'N 4N 1 ( pn( 4 Me CMe 3.7-1116, OAM j 1-1 I. 11.1. L. -1.1-1-1- I I.' I ', I. I j I I I ' I. I ', I I I I I I I 180 160 140 120 100 80 60 40 20 0 ppm /giga/data/qtian/nmr/ctian.727.fid/1/pdata/1 unknown Fri May 24 21:54:14 1996

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. - - 1 ) r ) r ) r o 4 CD I SiMe 3 a] r- 4ne]r ~I.~ ~II' I I I* 1****[****1 S.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 ppm /giga/data/qtian/nmr/htian.720.fid/1/pdata/1 unknown Tue May 21 15:45:45 1996

m - O C> I-) ID-oc )r = -C I 0 - C n N ~ SIMe 3 180 10O 2 1 60 40 20 0 ppm /giga/data/qtian/nmr/ctian.753.fid/1/pdata/1 unknown Wed Jun 19 21:10:15 1996

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 04-1- - - 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 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 /giga/data/qtian/nmr/htian.791.fid/l/pdata/1 unknown Tue Jul 2 09:30:42 1996 ppm

(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 - -- 40 - ---- a r- - - -o -o 0o0- - 00 40)- (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 180 160 140 120 100 80 60 /giga/data/qtian/nmr/ctian.790.fid/1/pdata/1 unknown Wed Jul 3 22:28:58 1996, I.1'.. I ' ' ' ' 4 40 20 0 ppm

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