ࡱ> !d"bjbjޥ 4*ǴǴ2nn4<F$::::$4 L-::SSS::SSSS:W?;|S 0<S K S S<S~< n :SINTEZA I REKACIJE U POBUENOM STANJU TIOFENSKIH I PIRIDINSKIH DERIVATA BUTADIENA SYNHESIS AND EXCITED STATE REACTIONS OF THIOPHENE AND PYRIDINE DERIVATIVES OF BUTADIENE Ivana `agud1, Marko Leva i, Dragana Vuk1, Irena `kori1 11)Zavod za organsku kemiju, Fakultet kemijskog in~enjerstva i tehnologije, Sveu iliate u Zagrebu, Maruliev Trg 19, 10 000 Zagreb, Hrvatska isagud@fkit.hr Unutar naae grupe detaljno je studirana reaktivnost raznih butadienskih derivata. Energija potrebna za reakcije dovedena je fotokemijskom pobudom [1,2] ili termi kim putem [3,4]. Pri tome su studirani butadienski derivati pokazali raznoliko ponaaanje u pobuenom stanju a izolirani su i u potpunosti okarakterizirani novi bicikli ki produkati do kojih bi klasi nom sintezom teako bilo doi. Biciklo[3.2.1]oktanski kostur koji je bio naj eai produkt u reakcijama butadiena u pobuenom stanju je prisutan u velikom broju bioloaki aktivnih spojeva izoliranih iz prirode [5]. Zbog toga je odlu eno istra~ivanje ovih reakcija proairiti na derivate u kojima e benzensku jezgru zamijeniti heterocikli ka. Do sada smo uspjeano sintetizirali derivate s tiofenskom i piridinskom jezgrom.  EMBED ChemDraw.Document.6.0  Sintetizirani su 2- i 3-[4-(2-vinilfenil)buta-1,3-dienil]tiofeni te 3- i 4-[4-T V X n p t ɳsYD/s)h~]5B*CJOJQJ\^JaJph)ht5B*CJOJQJ\^JaJph2htht5B*CJH*OJQJ\^JaJph)hT 5B*CJOJQJ\^JaJph#hGJh]aT5CJOJQJ^JaJ1hGJhGJB*CJOJQJ^JaJmH phsH +hT B*CJOJQJ^JaJmH phsH #hGJB*CJOJQJ^JaJph#h]aTB*CJOJQJ^JaJph#hT B*CJOJQJ^JaJph V X b    d d`gd#i$d`a$gd $d`a$gd $d`a$gdt $a$gdGJ$a$gdGJ$a$gdT $dx7$8$H$a$gd6H| $7$8$H$a$gdGJ     麦qbP1%hxCJaJmHsH<hGJh]aTB*CJOJQJ\^JaJmHnHph# sHtH#hGJhGJ5CJOJQJ^JaJhT 5CJOJQJ^JaJht5CJOJQJ^JaJ#hT hT 5CJOJQJ^JaJ&hT hT 5CJH*OJQJ^JaJ&htht5CJH*OJQJ^JaJ2hT h6H|5B*CJH*OJQJ\^JaJph)hT 5B*CJOJQJ\^JaJph,hT 5B*CJH*OJQJ\^JaJph  T V X n   0 4 b d f h n $ & 8 : < > B J ~ Rz|J^ "\^پپپپ+jF"Z h%^5h'CJUVaJmHsH%jh%^5h#iCJUaJmHsHh%^5h%^5CJaJmHsHh%^5h'CJaJmHsHhpCJaJmHsHh%^5CJaJmHsHhsCJaJmHsHh%^5h#iCJaJmHsH0^`bdfLjv 48LNrNʾʮ}}}}p`P``h%^5hFCJ\aJmHsHh%^5hZ(XCJ\aJmHsHhpCJ\aJmHsH"h%^5h#i6CJ\aJmHsHhFCJ\aJmHsHUh%^5h'CJ\aJmHsHh%^5h#iCJ\aJmHsHhFCJaJmHsHh%^5h#iCJaJmHsH%jh%^5h#iCJUaJmHsH%jh%^5h CJUaJmHsH(2-vinilfenil)buta-1,3-dienil]piridini. S obzirom na vrstu sinteze nastaju dva izomera svakog spoja i to cis,cis- i cis,trans-izomer koji su razdvojeni i u potpunosti okarakterizirani. Provedena su istra~ivanja reakcija u pobuenom stanju te su razdvojeni i okarakterizirani svi novi bicikli ki te tricikli ki fotoprodukti. 1. I. Kikaa, I. `kori, M. Kovacs, L. Fodor, }. Marini, K. Mol anov, B. Koji-Prodi, O. Horvath, J. Org. Chem. 76 (2011) 8641. 2. D. Vuk, O. Horvath, }. Marini, I. `kori, J. Mol. Struct. 1107 (2016) 70. 3. I. `kori, F. Pavoaevi, }. Marini, M. `indler, M. Eckert-Maksi, M. Vazdar, D. Margeti Org. Biomol. Chem. 9 (2011) 6771. 4. D. Vuk, }. Marini, K. Mol anov, D. Margeti, I. `kori Tetrahedron 70 (2014) 886. 5. D. C. Ericsson, L. E. Cuca, M. Sefkow, J. Nat. Prod. 72 (2009) 1245. NltRl ( * , !(!*!!!!!!Źvnf[Oh#ih#i6CJaJh#ihpCJaJhy4CJaJhzxCJaJhzxhx6CJaJhxCJaJhpoCJaJhpCJaJh#iCJaJhBh#i6CJaJh#ih#iCJaJh#ihZ(XCJ\aJh%^5h#iCJ\aJmHsHh%^5hZ(XCJ\aJmHsHh8CJ\aJmHsHh9CJ\aJmHsH* (!!d"dgdZ(XgdZ(X!!!!""$"B"b"d"hZ(Xh$CJaJhBh#i6CJaJhACJaJhpCJaJh#ih#iCJaJhBCJaJ 21h:pGJ. A!"#/ $/ % Dd zIb  c $A? ?3"`?"C}CNЫZ&D@=}CNЫZ&dg_F5 x] xEڮ $d@  .AT0!@ $$%GsH@XT< nPDA]UW4=]m&qwz~#B|1;Kh"DX!o# BxdE +'h_zDWxa5{D-aĒl61bOJ(3K7rt[햛,d-P6-҅7J/*&]8,`2LYՖ9ǭq(VNc5x-ڟnbޢ~Uu1a<'L9eʕsm3\<kCWbW˸VԳOEK.c_#D!x\jKq*3vw9 & :^|Xs_=W^k}Wt̸s/WeXW9$M`dh{Ox5 Oa3V6?[=#IϚF$\ܢ ؐ7sT*yv'z7s =ߖ0YσԲ! e$ /u/lx:<߀z&LjF$xy~yPaXLMnvx.6gz:kp>pK=sL-s zӘj]Gs]u]#>?NY_yLyP爌% uabE)>gj53g>y 'DNqߖɬEǮ{SԶT-J+UʭNT}תamR_xJ=^o;W ݣU5TQ&e)PQ׿Wzs{oTcW]g+egU5K6,R,SWy}U/SOuWej韪f?d?vlao͏T_b= TnDZJSGW/SO>kOWmvN4UuVQC{ޯFמ?:[%|3S%.>2C5Y6]mk~|:%*qfp}4fzբUl$5vƶ)}sG&W ?-gFp߁5Q7ŜƇF+jj#lSFޯo埌sSg1:1 玴By2*2kC-䙿0=w$</ܑ.3[c& =P 8@:ic︳0T؟s~lZš|Rf:إwRWKCyNYcLBk= Y/vvBhcfwMTzôXނŰ90jQzP55+Ǥ #ui05.S6T?x_@Nv $Ӝ7[[F 0+qKc_5rj]A7x^|XLQX<-zύT-j2$J`ae9Y k5R8;2:Fu˻b9=oF=Vqq .mq+?}a3Qj 7m0Əqim$usݾRêè?jyCuɳwڔ滟61J=5gr<[#"y x_k} zy66F|wq}r$ʫ/=``w‚tC/U Ϝ#ପ| "3nh3|:8 9[I9NK]68ec~=Q%mtZ|`D]ƪ /4k^\Yf,1ϽWM]b9QTi.z44i6CM}LYYCgVwO]9C04{3R_'MS%sO3&gOUWgy>by~wmQk^0upyFL"qֿn{'Ɨq8?ail4EcIck~C$'u,W9~`tKqo m~S&[2ş.^SmRK婤NlR_'&E0=w|:;r#k!oe9wLyƞ;0Zۓg,zu/ v)-:kpYrov<ߊkN,N~7E;C J.qc8=Rō\5|;]^lFQ\SSl``W#1={;P=Hr4ku@ ~ٷ_S`8|&L:~JޗQFϴF)Zw+jF,&."6'皗>`b=u<@f]>ϴ\{wgjyPJd{QTbqʎ6V;3RϧS1N4o#og<ұ:ex^ צtH?T 7|znApF{p8?@ABCRoot Entry  F?;"Data WordDocument 4*ObjectPool W?;?;_1512195786!mA. W?;W?;Ole CompObj~ObjInfo  !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.6.09q Oh+'0l   ( 4 @LT\dSAETAKxxCONTENTS$1Table3 SummaryInformation( DocumentSummaryInformation8 DVjCD0100ChemDraw 11.0.1Microsoft Word - agud.doco5  gfo ̅33 :;E<  BCD8 `  fx# $$$$2Arialx  f g'  fdd'`$o7&C$$>o5j=c}M O7-M P75, Q7-W= R}W= SJ, T75' [7}-4 \7J' ]7}M a7J٥@ b7--4 o7}c 7 U  V  W  X  Y  Z  ^  _  `  c  d  p  OG̙5$G q7-G r74s s7- t$ us v74ʁ }7$ ~7ʁ 7$L 7 r 7- 7 7 w  x  y  z  {  |              0Y &"pJ0Y e2This atom is very close to another atom or bond.7 &f f+7p "acac &"j# `Sr_p g7,i h7 {[ i7 j  k  l  m  n w} wb 2This atom is very close to another atom or bond.7$ 7R  +7OͺǏͺO # `N R  7X 7 wb 7            ^HDS/߼VxbcC_8,;@СYkk8+x'&܄`f*EMelD{)nLn˸F96ƋfC0ǍK_yvᅗ煴kNj6ˆᙤl?> ީR|Ys{ypЃ1}v#䊘6 x8&cV,yl 9@^ e}}2<4S2Dg;ح E:$w=.Mw(3RxOP ^@!Q2.I5<AG$[i= 0[ƴID)xsZg R1}iP|(zG4&.쎊vYKq*najibú0D#0,xL#nvE_aь]+0I PLЩ6"I]6"q ֦۰+Vhc˫[ONUʹ-Y{} zD|T#;i,; [ eǰ]OBm)p1K>9;3 [ vƁ BrzSl}sv/ [ r;8 +FutPW[^ƆCn3g1gC&/1?u 3e'qiYmV{h~Tj+L iAQj; ;GaLz [ƶDCE-ZOv*萼v?uM6 +{FÊDloa5 V>gƸ0ƶ-aiĽ!g5nWc];4 #z}ak6lJE Na[5 :6"E @16"% [zls*^v` b?+YF s1QԐ}˨m;i,2> [ e|%E|!}pb</(!ں)!1g1gB5/j@7P*ЅtBTʍ ncY9!^ؚ^xbn):n8S{Ŝ“ps} J*]CZΗقC3}aLڏ-c5Qْ"wĒW:@mX;G~>'{Q2&odءyCcCF> x4 pwިn`yq+l{ٮs11"ɯTOu%ƜX]OG͹F4[pc!Ete7=kΌ'Xgc:qzЁW8s6"Ŋ.oFÀB4Zr EZ O#D{\olB(,\@sCjI0<ѹNGbGxakzቺuBjK\GpL'QRoF~NM ۨZqwx믔;rV]-3<$i j^]ïDyxje7ΝPՖlϋQaw- F/F]w@ !&\t ೘!^ؚ^ȝG(!C^~ v:,=;\Ⅽ酼D j ,Xc{p߁>oh}~ߢGPQ  KY<]QVD@dNormal korisnik27Microsoft Office Word@NSI@0-;@s;@S>;9՜.+,0 hp|  HP. SAETAKSAETAK TitleNaslov  F Microsoft Word 97-2003 Document MSWordDocWord.Document.89q^ 666666666vvvvvvvvv666666>6666666666666666666666666666666666666666666666666hH6666666666666666666666666666666666666666666666666666666666666666662 0@P`p2( 0@P`p 0@P`p 0@P`p 0@P`p 0@P`p 0@P`p8XV~_HmHnHsHtH\`\ *{Normal35B*CJFOJQJ\^J_HaJFmHph# sHtHn@n *{ Heading 1$<1$@&-B*CJ KH OJQJ^JaJ mH phsH tH DA D Default Paragraph FontRiR  Table Normal4 l4a (k (No List fB@f *{ Body Text x1$/5B*CJOJQJ\^JaJmH phsH tH PK![Content_Types].xmlN0EH-J@%ǎǢ|ș$زULTB l,3;rØJB+$G]7O٭V$ !)O^rC$y@/yH*񄴽)޵߻UDb`}"qۋJחX^)I`nEp)liV[]1M<OP6r=zgbIguSebORD۫qu gZo~ٺlAplxpT0+[}`jzAV2Fi@qv֬5\|ʜ̭NleXdsjcs7f W+Ն7`g ȘJj|h(KD- dXiJ؇(x$( :;˹! I_TS 1?E??ZBΪmU/?~xY'y5g&΋/ɋ>GMGeD3Vq%'#q$8K)fw9:ĵ x}rxwr:\TZaG*y8IjbRc|XŻǿI u3KGnD1NIBs RuK>V.EL+M2#'fi ~V vl{u8zH *:(W☕ ~JTe\O*tHGHY}KNP*ݾ˦TѼ9/#A7qZ$*c?qUnwN%Oi4 =3N)cbJ uV4(Tn 7_?m-ٛ{UBwznʜ"Z xJZp; {/<P;,)''KQk5qpN8KGbe Sd̛\17 pa>SR! 3K4'+rzQ TTIIvt]Kc⫲K#v5+|D~O@%\w_nN[L9KqgVhn R!y+Un;*&/HrT >>\ t=.Tġ S; Z~!P9giCڧ!# B,;X=ۻ,I2UWV9$lk=Aj;{AP79|s*Y;̠[MCۿhf]o{oY=1kyVV5E8Vk+֜\80X4D)!!?*|fv u"xA@T_q64)kڬuV7 t '%;i9s9x,ڎ-45xd8?ǘd/Y|t &LILJ`& -Gt/PK! ѐ'theme/theme/_rels/themeManager.xml.relsM 0wooӺ&݈Э5 6?$Q ,.aic21h:qm@RN;d`o7gK(M&$R(.1r'JЊT8V"AȻHu}|$b{P8g/]QAsم(#L[PK-![Content_Types].xmlPK-!֧6 0_rels/.relsPK-!kytheme/theme/themeManager.xmlPK-!0C)theme/theme/theme1.xmlPK-! ѐ' theme/theme/_rels/themeManager.xml.relsPK] 2*  ^N!d" d" 2:8@0(  B S  ?MX S\0>nx{ &OVilmptw~*56BLQ&/SY^diqw} 4Q01qsD"1433 1234JKLL[\%/5;AB':CDE 114 1234JKLL[\%/5;AB':CD 114IHF)tID  \ '1%^5I9:U;Ta>c>aL?B.bD2JGJ4NP^(S]aTAUZ(Xi]~]cd7e"h#ipopttzx6H| 9Ap>!T Ruy &*{ l3x; 8m"Xyx){sCDy46z"$H{DM24@(2 UnknownG* Times New Roman5Symbol3. * ArialMMinionPro-BoldSubhA$BCambria Math"q\<'<'h<'-99%/ 24..3qHX ?*{2!xx SA}ETAKxxkorisnikCompObjr