(C) ACD $$.RPT.( V 2.0 )>o ??o,OArial,Arial,Arial,Arial,Arial, Arial,Times,Times,Times,Times,Times,Times,Times, ^ CCDEuC@DECCCDECCCDECAFT )Sample E13 (E:A-13), Spring 2003 Unknownsr 8EuCEEC>EC8EuCEEuC8EuCEEuCAFT 21 Mar 2003s 8ECEEC>EC8ECEEC8ECEECAFT D. R. Mowreyp &CCDCUCC&CCDC&CCDCAFTq Name Codej VDCVDCVU DCVDCVDCVDCVDCAFT<E13l i;DCԋDCiDCi;DCԋDCi;DCԋDCAFTqClassr -ʉDC-DC-ڔDC-ʉDC-DC-ʉDC-DCAFT Spring 2003i YDCYDCYDCYDCYDCYDCYDCAFTqFWo DCDC9DCDCDCDCDCAFT180.2005n sDCECAECsDCECsDCECAFTqFormula ECDECEC ECDEC ECDECAFTC10H12O3q &CCDCUCC&CCDC&CCDCAFTq Solvent(s) VDCVfDCVU4DCVDCVfDCVDCVfDCAFTCDCl3 with ~2 drops MeODz YDCYDCYDCYDCYDCYDCYDCAFTqMass of Sample Usedn DCDCDCDCDCDCDCAFTw32.1 mgq sDCECAECsDCECsDCECAFTq Mass Spec.y ECdECEC ECdEC ECdECAFT179.0 [-1]_____ESIv &CCDCUCC&CCDC&CCDCAFTqMass Spec Log #k VDCVUDCV DCVDCVUDCVDCVUDCAFTJ0163r i;DCԋDCiDCi;DCԋDCi;DCԋDCAFTq Operator(s)r -ʉDC- DC-jDC-ʉDC- DC-ʉDC- DCAFT Dale Mowreyk YDCYDCYDCYDCYDCYDCYDCAFTqm.p.t DCDCDCDCDCDCDCAFT 129.5-130.5 Cu )EC93EC'EC)EC93EC)EC93ECAFTqSynthesized byw Y42ECYdAECY9ECY42ECYdAECY42ECYdAECAFTW.R. Biggerstaffp &CCDDUCC&CCDC&CCDCAFTq Key Wordsj VDCVDDVDCVDCVDCVDCVDCAFT8???l i;DCԋDDiDCi;DCԋDCi;DCԋDCAFTqNotesk -ʉDC-DD-DC-ʉDC-DC-ʉDC-DCAFTNNone4CC?7DC?7DCCC 4?7DCDCDC?7DC 4DC^DC^DCDC 4^DCECEC^DC 4CCDCDCCC 4DC^DC^DCDC 4^DCDECDEC^DC 4CC?7DC?7DCCC 4?7DCDCDC?7DC 4DCECECDC 4ECDECDECEC 4CC?7DC?7DDCD 4?7DCDCDD?7DD } &C@ D*DDVշCD&C@ D*D@ D&C@ D*D@ DAFTAcquisition Time (sec)m V D@ DVU#DDVDDV D@ DVU#D@ DV D@ DVU#D@ DAFTe1.5729n 13C{ ED5E@ Dm)EDED5EDED5EDAFTNumber of Transientsj 4EDx8E@ D6ED4EDx8ED4EDx8EDAFT8192| &C@ D*D+DVշC&D&C@ D*D@ D&C@ D*D@ DAFTOriginal Points Countl V D@ DV!D+DVD&DV D@ DV!D@ DV D@ DV!D@ DAFT\32768s BE=B7B2BB B$پB5B)BxBKNB,̺B:BĺB\zBB/BBUBSzBS:B ^B_Bm.BBBBBPB B/оBBӾB޹B1ByBLBB,оB~BBeBB5OBBr1B*B'BJտBBHBBTBzB|B:ϸBٿBB5BBl=BgzBnԾBbBȿBQFBlB)B,BBBBjƾBB/B߷B:վBBmB.BBĐBKB\BBSBGBCRBqB+BBBBvBIB B BĶBʨBBkBB{BΐBe|BhBBVB8Bx=B=BBB B'EBB@(BFصBBYϵBnBB)B1B6BIBhBtB\BjIBUBBBBBB)sB[BhBBxLB-BBB BBBB߲B;BBBBNBꖲBBBBzBBhB;BKB BB-BZBByBBBcޱB>BuձBDBBBYB 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B-AB-AZBʭ,AB,AB+A>mB+*ABB*A6B%)AKB(AB`'AeB['A,B+&ARB<%ABBP$A6Bx#AB(1#AB"AB A7¾Ba A\B/AsBlA'BABVAGjB$ABA49Br1A$BAUeBA2nB A箾B,gA#LBɜA yBA0BAƻBA陾Be[ABA\BABCAyBZA!BYABABA սBAB:A1(B0 A?B A!BC ABL AB ABi AXB.2 AHB[AvBA8BA*BIAIBA"BzA$BAB bAB,AX¾BABPPAMB܂@Bx@BƠ@cB;@JBG@'Ba@B@|B*@BK @ΦB_@'BY@ꔾB@7B@B4@fBG@\|BF@B@8_Bk@~B0`@@\Bg@SBӸ@^BV@5۾Bۋ@pB@B8@TBwJ@% B@xB'@B@4Bsn@A]B%@EBt@B]@Bz@Bo@GB@4B@B@ B@MB0]@V B@BB@B'@BK@B@@SBzi@Bg@#BW@uB@ɥB΋@B@gBv@9Bu@BM:@BLÅ@B@BJR@9B"@<Bv@B|@GB]x@lBv@B)s@!B"n@pBm@ĽB™j@־B_Rf@SBHb@#Ba@iBZ^@!B1\@8BW@KBT@BS@+BɎP@8^BdYK@{{BuH@&BtE@"B8B@-BMA@͒B<@ɝB;@lB08@ :B 2@BN1@S9B6-@oRBl*@l]B`(@ھBC'@rB:"@-B!@B+@kB @eBpa@֛B"e %CR+@?##BEBBEBc)B_:B 11.89(10)#ZʝB%NBZʝB%NBc)BS1B26.27(9)#ËBgBËBgBc)BoB52.41(8)#@B@@B@c)B/2B 115.23(6, 2)#\.Ba@\.Ba@c)BWfB 128.89(5, 3)#">,BzB">,BzBc)BкA 130.23(4)#PZ BV>BPZ BV>Bc)B4A 155.53(1)#|AbGB|AbGBc)BA 177.55(11)SBSB)B Methanol-d4quBquB]B Chloroform-dC@DDEDC DDED Chemical Shift (ppm) Intensity  ;CD D E"No.(ppm)(Hz)Height 111.89896.60.4973226.271980.60.4731352.413952.30.40674115.238689.00.99895128.899718.31.00006130.239819.40.28117155.5311727.50.23978177.5513387.60.1968@DD EE No.AtomExp. Shift (ppm) 11155.5322115.2333128.8944130.2355128.8966115.237852.418926.2791011.891011177.55u ??u,NArial,Arial,Arial,Arial,Arial,Arial,Symbol,Times New Roman,Times New Roman, Arial,Times,Times,Times,Times,Times,Times,Times, ^CCDEuC@DECCCDECCCDECAFT )Sample E13 (E:A-13), Spring 2003 Unknownsr8EuCEEC>EC8EuCEEuC8EuCEEuCAFT 21 Mar 2003s8ECEEC>EC8ECEEC8ECEECAFT D. R. Mowreyp &CCDCUCC&CCDC&CCDCAFTq Name CodejVDCVDCVU DCVDCVDCVDCVDCAFT<E13l i;DCԋDCiDCi;DCԋDCi;DCԋDCAFTqClassr-ʉDC-DC-ڔDC-ʉDC-DC-ʉDC-DCAFT Spring 2003i YDCYDCYDCYDCYDCYDCYDCAFTqFWoDCDC9DCDCDCDCDCAFT180.2005n sDCECAECsDCECsDCECAFTqFormula  ECDECEC ECDEC ECDECAFTC10H12O3q &CCDCUCC&CCDC&CCDCAFTq Solvent(s)VDCVfDCVU4DCVDCVfDCVDCVfDCAFTCDCl3 with ~2 drops MeODz YDCYDCYDCYDCYDCYDCYDCAFTqMass of Sample UsednDCDCDCDCDCDCDCAFTw32.1 mgq sDCECAECsDCECsDCECAFTq Mass Spec.y ECdECEC ECdEC ECdECAFT179.0 [-1]_____ESIv &CCDCUCC&CCDC&CCDCAFTqMass Spec Log #kVDCVUDCV DCVDCVUDCVDCVUDCAFTJ0163r i;DCԋDCiDCi;DCԋDCi;DCԋDCAFTq Operator(s)r-ʉDC- DC-jDC-ʉDC- DC-ʉDC- DCAFT Dale Mowreyk YDCYDCYDCYDCYDCYDCYDCAFTqm.p.tDCDCDCDCDCDCDCAFT 129.5-130.5 Cu )EC93EC'EC)EC93EC)EC93ECAFTqSynthesized bywY42ECYdAECY9ECY42ECYdAECY42ECYdAECAFTW.R. Biggerstaffp &CCDDUCC&CCDC&CCDCAFTq Key WordsjVDCVDDVDCVDCVDCVDCVDCAFT8???l i;DCԋDDiDCi;DCԋDCi;DCԋDCAFTqNotesk-ʉDC-DD-DC-ʉDC-DC-ʉDC-DCAFTNNone4CC?7DC?7DCCC 4?7DCDCDC?7DC 4DC^DC^DCDC 4^DCECEC^DC 4CCDCDCCC 4DC^DC^DCDC 4^DCDECDEC^DC 4CC?7DC?7DCCC 4?7DCDCDC?7DC 4DCECECDC 4ECDECDECEC 4CC?7DC?7DDCD 4?7DCDCDD?7DD } &C@ D*DDVշCD&C@ D*D@ D&C@ D*D@ DAFTAcquisition Time (sec)mV D@ DVU#DDVDDV D@ DVU#D@ DV D@ DVU#D@ DAFTe2.7197n ڤ:D@ DmDDlDDڤ:D@ DmD@ Dڤ:D@ DmD@ DAFTCommento‡D@ D§DD—DD‡D@ D§D@ D‡D@ D§D@ DAFTEA13.001k ϥD@ DDDDDϥD@ DD@ DϥD@ DD@ DAFTDate{D@ DڄDDDDDD@ DڄD@ DD@ DڄD@ DAFT415/01/2003 02:51:43p &CD*D@ DVշCD&CD*DD&CD*DDAFT File Name|V DDVcD@ DV6DDV DDVcDDV DDVcDDAFTdE:\E-A13\E-A13_1H.001v ϥDDD@ DDDϥDDDDϥDDDDAFTFrequency (MHz)mDDڤD@ DTDDDDڤDDDDڤDDAFTe299.87n LDDNFE@ DNEDLDDNFEDLDDNFEDAFTNucleusi@EDE@ DED@EDED@EDEDAFT,1H{ dEDڄ4E@ D'EDdEDڄ4EDdEDڄ4EDAFTNumber of Transientsi3ED5E@ D4ED3ED5ED3ED5EDAFT&16| &C@ D*D+DVշC&D&C@ D*D@ D&C@ D*D@ DAFTOriginal Points CountlV D@ DV!D+DVD&DV D@ DV!D@ DV D@ DV!D@ DAFT\16384s ڤ:D@ DmD+DlD&Dڤ:D@ DmD@ Dڤ:D@ DmD@ DAFT Points Countl‡D@ DD+DGD&D‡D@ DD@ D‡D@ DD@ DAFT\32768w ϥD@ DD+DD&DϥD@ DD@ DϥD@ DD@ DAFTSweep Width (Hz)nD@ DD+DtD&DD@ DD@ DD@ DD@ DAFTw6024.10} LD@ DNFE+DNE&DLD@ DNFE@ DLD@ DNFE@ DAFTTemperature (degree C)m@E@ DE+DhE&D@E@ DE@ D@E@ DE@ DAFTe24.0004C@ D/z6D@ D/z6DDCD 4/z6D@ D/D@ D/DD/z6DD 4/D@ D/ZE@ D/ZED/DD 4CD/DD/D@ DC@ D 4/DDF7DDF7D@ D/D@ D 4F7DD/ZED/ZE@ DF7D@ D 4/ZEDDEDDE@ D/ZE@ D 4C@ D/z6D@ D/z6D+DC+D 4/z6D@ D/D@ D/D+D/z6D+D 4/D@ DF7D@ DF7D+D/D+D 4F7D@ D/ZE@ D/ZE+DF7D+D   C2DEEPDD@AD C2DEE2D C2DEE2DAFT   1H NMR (300 MHz, Solvent) d  ppm 0.9 (t, J=7.4 Hz, 3 H) 1.7 (m, J+=13.8, 7.4, 7.4, 7.4, 7.4 Hz, 1 H) 2.0 (m, J'=13.8, 7.4, 7.4, 7.4, 7.4 Hz, 1 H) 3.4 (t, J=7.5 Hz, 1 H) 6.8 (d, J=8.5 Hz, 2 H) 7.1 (d, J =8.6 Hz, 2 H)$/?3*(EED1$/?2*(EW-D1$/?4 %ExD1$/?1 %E/!D1$/?5!EED1$/?6!EW-D1$/?8 %E4hD1$/?7 %ED1%/?11(Em`D1$/?9|!E`D1%/?12Z+EhD1%/?10v!E6QD1%/?13(E QD1%/?9aӾE*mD1%/?9bE=1_D1/? 5 /?W  /?W Z B/?" 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@2.00#ZBŪBZBŪBBx@A2.02#uB-BuB-BBA2.04#\B~CB\B~CBBxA2.05#w!BQBw!BQBBx`A2.07#B>BB>BB@2.09#:B:AB:B:ABB,?2.12#rBk5BrBk5BBDMA3.33#qB@BqB@BBsA3.35#'pB(OB'pB(OBB(vDA3.38#OA]BOA]BBٓ@6.75#AwFBAwFBBD?B6.76#A2BA2BBڋA6.76#tAWBtAWBBXA6.78#ABABBeB6.78#+AAB+AABB V@6.79#aA8BaA8BB0V@7.12#A/BA/BB.&VB7.13#QA0BQA0BBA7.14#4AB4ABB{A7.15#:A;LB:A;LBB9B7.16#= AkݵB= AkݵBB @7.17߭B߭BTBTMS~A~AqB ChloroformBB<@M00(10)pBrB@BM03(8)َAA/B M06(5, 3)ANAB M04(6, 2)oBbBŪBM01(9a)$BBJBM02(9b)C@DDE0 EC@DDEE#ED%E= E ~BF%ABXAhBFAJ Ba%B,B{NBAFxB[AӐBzAeBW?4BO2>wD@ТBBfEE`EK EfBY@5B`A FBATBA B BiB(B/SkBDB2HB`B B#|BABBjAB?ABÇ\@BPj@BX{>?B}wBAETE=EQ E8B|B@|TBA_AB^qABAA>B B+3B>q'BBmYCBP_^BA_B0|+B){B;) BB'A}BswA.qB@FeBH@^YBk>4~?"BbB:DxElD] E 9By=AzByABBBky=B07BlB$AB~A/ʥBh@WyB:>~?oBN>sB~DEDELD E4BMAB>A9BHB"nBMB><4B"BOAHB>@BR>?A}AUeD0 EIkD E(9BQPARBA1IB߅BzBePB2LBuoBOBB.E@B1>w@vAA Chemical Shift (ppm) Intensity  % ??%, MArial,Arial,Arial, Arial,Times,Times,Times,Times,Times,Times,Times, ^ CCDEuC@DECCCDECCCDECAFT )Sample E13 (E:A-13), Spring 2003 Unknownsr8EuCEEC>EC8EuCEEuC8EuCEEuCAFT 21 Mar 2003s8ECEEC>EC8ECEEC8ECEECAFT D. R. Mowreyp&CCDCUCC&CCDC&CCDCAFTq Name CodejVDCVDCVU DCVDCVDCVDCVDCAFT<E13li;DCԋDCiDCi;DCԋDCi;DCԋDCAFTqClassr-ʉDC-DC-ڔDC-ʉDC-DC-ʉDC-DCAFT Spring 2003iYDCYDCYDCYDCYDCYDCYDCAFTqFWoDCDC9DCDCDCDCDCAFT180.2005nsDCECAECsDCECsDCECAFTqFormula ECDECEC ECDEC ECDECAFTC10H12O3q&CCDCUCC&CCDC&CCDCAFTq Solvent(s)VDCVfDCVU4DCVDCVfDCVDCVfDCAFTCDCl3 with ~2 drops MeODzYDCYDCYDCYDCYDCYDCYDCAFTqMass of Sample UsednDCDCDCDCDCDCDCAFTw32.1 mgqsDCECAECsDCECsDCECAFTq Mass Spec.y ECdECEC ECdEC ECdECAFT179.0 [-1]_____ESIv&CCDCUCC&CCDC&CCDCAFTqMass Spec Log #kVDCVUDCV DCVDCVUDCVDCVUDCAFTJ0163ri;DCԋDCiDCi;DCԋDCi;DCԋDCAFTq Operator(s)r-ʉDC- DC-jDC-ʉDC- DC-ʉDC- DCAFT Dale MowreykYDCYDCYDCYDCYDCYDCYDCAFTqm.p.tDCDCDCDCDCDCDCAFT 129.5-130.5 Cu)EC93EC'EC)EC93EC)EC93ECAFTqSynthesized bywY42ECYdAECY9ECY42ECYdAECY42ECYdAECAFTW.R. Biggerstaffp&CCDDUCC&CCDC&CCDCAFTq Key WordsjVDCVDDVDCVDCVDCVDCVDCAFT8???li;DCԋDDiDCi;DCԋDCi;DCԋDCAFTqNotesk-ʉDC-DD-DC-ʉDC-DC-ʉDC-DCAFTNNone4CC?7DC?7DCCC 4?7DCDCDC?7DC 4DC^DC^DCDC 4^DCECEC^DC 4CCDCDCCC 4DC^DC^DCDC 4^DCDECDEC^DC 4CC?7DC?7DCCC 4?7DCDCDC?7DC 4DCECECDC 4ECDECDECEC 4CC?7DC?7DDCD 4?7DCDCDD?7DD }&C@ D*DDVշCD&C@ D*D@ D&C@ D*D@ DAFTAcquisition Time (sec)mV D@ DVU#DDVDDV D@ DVU#D@ DV D@ DVU#D@ DAFTe2.7197nڤ:D@ DmDDlDDڤ:D@ DmD@ Dڤ:D@ DmD@ DAFTCommento‡D@ D§DD—DD‡D@ D§D@ D‡D@ D§D@ DAFTEA13.001kϥD@ DDDDDϥD@ DD@ DϥD@ DD@ DAFTDate{D@ DڄDDDDDD@ DڄD@ DD@ DڄD@ DAFT415/01/2003 02:51:43p&CD*D@ DVշCD&CD*DD&CD*DDAFT File Name|V DDVcD@ DV6DDV DDVcDDV DDVcDDAFTdE:\E-A13\E-A13_1H.001vϥDDD@ DDDϥDDDDϥDDDDAFTFrequency (MHz)mDDڤD@ DTDDDDڤDDDDڤDDAFTe299.87nLDDNFE@ DNEDLDDNFEDLDDNFEDAFTNucleusi@EDE@ DED@EDED@EDEDAFT,1H{dEDڄ4E@ D'EDdEDڄ4EDdEDڄ4EDAFTNumber of Transientsi3ED5E@ D4ED3ED5ED3ED5EDAFT&16|&C@ D*D+DVշC&D&C@ D*D@ D&C@ D*D@ DAFTOriginal Points CountlV D@ DV!D+DVD&DV D@ DV!D@ DV D@ DV!D@ DAFT\16384sڤ:D@ DmD+DlD&Dڤ:D@ DmD@ Dڤ:D@ DmD@ DAFT Points Countl‡D@ DD+DGD&D‡D@ DD@ D‡D@ DD@ DAFT\32768wϥD@ DD+DD&DϥD@ DD@ DϥD@ DD@ DAFTSweep Width (Hz)nD@ DD+DtD&DD@ DD@ DD@ DD@ DAFTw6024.10}LD@ DNFE+DNE&DLD@ DNFE@ DLD@ DNFE@ DAFTTemperature (degree C)m@E@ DE+DhE&D@E@ DE@ D@E@ DE@ DAFTe24.0004C@ D/z6D@ D/z6DDCD 4/z6D@ D/D@ D/DD/z6DD 4/D@ D/ZE@ D/ZED/DD 4CD/DD/D@ DC@ D 4/DDF7DDF7D@ D/D@ D 4F7DD/ZED/ZE@ DF7D@ D 4/ZEDDEDDE@ D/ZE@ D 4C@ D/z6D@ D/z6D+DC+D 4/z6D@ D/D@ D/D+D/z6D+D 4/D@ DF7D@ DF7D+D/D+D 4F7D@ D/ZE@ D/ZE+DF7D+D $P%? 3NE~D1$P%? 2NEpD1$P%? 4ED1$P%? 1ED1$P%? 5 E~D1$P%? 6 EpD1$P%? 8ܠE2D1$P%? 7ݠE /D1%P%? 11NEgD1$P%? 9 E~D1%P%? 12|E2D1%P%? 10 EytD1%P%? 13NEatD1%P%? 9a ED1%P%? 9bI E=D1P%? E E P%?  _9 wP%?  9 P%? r ZP%?   GP%?  P%?   P%? P%? <  P%?  P%? t S P%? E E P%? P%? P%?  CDDDeMNo.Atom1 Multiplet1 Shift1 (ppm) (ppm)J (Hz)TypeH's 110M000.89[0.86 .. 0.91]7.35t3210M000.89[0.86 .. 0.91]7.35t339aM012.05[1.97 .. 2.12]7.35m149aM012.05[1.97 .. 2.12]7.35m159aM012.05[1.97 .. 2.12]7.35m169aM012.05[1.97 .. 2.12]7.35m179aM012.05[1.97 .. 2.12]13.79m189bM021.74[1.66 .. 1.83]7.35m199bM021.74[1.66 .. 1.83]7.35m1109bM021.74[1.66 .. 1.83]7.35m1119bM021.74[1.66 .. 1.83]7.35m1129bM021.74[1.66 .. 1.83]13.79m1138M033.35[3.32 .. 3.38]7.54t1148M033.35[3.32 .. 3.38]7.54t1156, 2M046.77[6.74 .. 6.80]8.46d2165, 3M067.15[7.12 .. 7.18]8.64d2  ??,Arial, Arial,CCDEuC@DECCCDECCCDECAFT )Sample E13 (E:A-13), Spring 2003 Unknownsr8EuCEEC>EC8EuCEEuC8EuCEEuCAFT 21 Mar 2003s8ECEEC>EC8ECEEC8ECEECAFT D. R. Mowrey\`DC@D0E2 No.(ppm)(Hz)Height &10.86258.30.433420.89265.71.000030.91273.00.484841.67500.80.015751.69508.20.064961.71514.20.043871.72515.50.106181.74521.80.105091.74522.50.0893101.76529.10.1345111.77530.60.0490121.79536.60.0823131.81544.00.0184141.97591.60.0205152.00599.00.0818162.02605.20.0493172.02606.50.1267182.04612.80.0859192.05613.90.1031202.07620.10.0976212.07621.60.0443222.09627.70.0611232.12635.00.0137243.33997.70.1350253.351005.50.2715263.381013.20.1292276.752023.00.0486286.762026.00.5030296.762027.80.1839306.782032.40.1840316.782034.40.6043326.792037.40.0836337.122135.40.0613347.132138.30.5632357.142140.30.1982367.152144.90.1690377.162147.00.4879387.172149.70.0684 DDED No.AtomExp. Shift (ppm)126.77237.15357.15466.77583.3569a2.0579b1.748100.89yDD@EDONo. Annotation (ppm) 1TMS0.002 Chloroform7.31O`DCPEPD%.No. (ppm)ValueAbsolute Value1[0.83 .. 0.94]3.064 1.14123e+82[1.66 .. 1.82]1.000 3.72421e+73[1.97 .. 2.12]0.993 3.69811e+74[3.31 .. 3.40]1.019 3.79679e+75[6.73 .. 6.82]1.976 7.35939e+76[7.10 .. 7.19]2.023 7.53383e+7