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Electronic upplementary Material (EI) for rganic Chemistry rontiers. This journal is the Partner rganisations 0 upporting Information Convenient ynthesis of Pentafluoroethyl Thioethers via Catalytic andmeyer Reaction with a table luoroalkylthiolation Reagent Christian Matheis, Bilguun Bayarmagnai, Kévin Jouvin and Lukas J. Gooßen* B Chemie rganische Chemie, TU Kaiserslautern, Erwin-chrödinger-tr. Geb., Kaiserslautern, Germany, ax: (+) -0-, E-mail: goossen@chemie.uni-kl.de.

Table of contents General Methods ynthesis of tarting Materials ynthesis of Pentafluoroethyl Thioethers from Arenediazonium alts pectroscopic Data

General Methods The reactions were performed in oven-dried glassware containing a Teflon-coated stirrer bar and septum under a nitrogen atmosphere. Acetonitrile were dried by refluxing over CaH and subsequent fractionally distillation. All reactions were monitored by GC and the yields were determined by NMR using trifluoroethanol as internal standard. GC analyses were carried out using a HP- capillary column (Phenyl Methyl iloxane 0 m x 0 x 0.) and a time program beginning with min at 0 C followed by 0 C/min ramp to 00 C, then min at this temp. Column chromatography was performed using a Combi lash Companion-Chromatography- ystem (Isco-ystems) and Grace Reveleris packed flash columns ( g). NMR spectra were obtained on a Bruker AMX 00 system using chloroform-d, acetonitrile-d or methanol-d as deuterated solvents, with proton, carbon and fluorine resonances at 00 MHz, 0 MHz and MHz, respectively. Mass spectral data were acquired on a Varian aturn 00 T. All commercially available starting materials were used without further purification. Me NC was commercially available by C Plus Chemicals s. r. o.

ynthesis of tarting Materials ynthesis of arene diazonium tetrafluoroborates In a 0 ml round-bottom flask, the aniline (0 mmol) was dissolved in a mixture of absolute ethanol ( ml) and an aqueous solution of HB (0%,. ml, 0 mmol) and tert-butyl nitrite (. ml, 0 mmol) was added dropwise to the solution at 0 C. The reaction was stirred at room temperature for h and diethyl ether (0 ml) was added to precipitate the arenediazonium tetrafluoroborate that was filtered off and washed with diethyl ether ( 0 ml). The arenediazonium tetrafluoroborate was dried in vacuo (0 - mbar) for 0 minutes and was then directly used without further purification.

ynthesis of pentafluoroethyl thioethers from arenediazonium salts tandard procedure: An oven-dried 0 ml crimp-cap vessel with stirrer bar was charged with Cu (. mg, 0.0 mmol), Me NC ( mg,.0 mmol) and MeCN ( ml). Then, the arenediazonium salt (.00 mmol) in MeCN ( ml) was added dropwise and the reaction mixture was stirred for h at room temperature. The resulting mixture was diluted with diethyl ether (0 ml). The organic solution was washed with water ( 0 ml) and brine (0 ml). The organic layer was dried over Mg, filtered and concentrated (00 mbar, 0 C). The residue was purified by flash chromatography (i, cyclohexane / ethyl acetate gradient), yielding the aryl pentafluoroethyl thioethers. The yields of particularly volatile compounds were determined by NMR, and their identity by mass spectroscopy. ynthesis of -methoxy--[(pentafluoroethyl)thio]benzene (a). Compound a was prepared following the standard procedure, starting from - methoxybenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, a was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =. (d, J =. Hz, H),. (d, J =. Hz, H),. ppm (s, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.0,.0 (C),.0 (C),. (t, J(C,) =. Hz), 0.0 (qt, J(C,) =.0 Hz, J(C,) = 0. Hz),. (tq, J(C,) =. Hz, J(C,) =.0 Hz),. ppm; IR (neat): =,,,,,, 0, 0, 0, 00,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), (00), (), (); HRM (EI-T) calcd. for C H :.0; found:.0. ynthesis of -methyl--[(pentafluoroethyl)thio]benzene (b). Compound b was prepared following the standard procedure, starting from -methylbenzenediazonium tetrafluoroborate (0 mg,.00 mmol). After purification, b was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.-. (m, H),.-. (m, H),. ppm (s, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),.0 ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,.,.,.,. (t, J(C,) =. Hz), 0. (qt, J(C,) =. Hz, J(C,) = 0.0 Hz),. (tq, J(C,) =. Hz, J(C,) =. Hz),. ppm; IR (neat): = 0,,,, 0, 0, 0,, 0, 0, cm - ; M

(Ion trap, EI, 0 ev): m/z (%) = [M + ] (00), (), (), (); HRM (EI-T) calcd. for C H :.0; found:.0. ynthesis of -[(pentafluoroethyl)thio]-,'-biphenyl [CA No.: --] (c). Compound c was prepared following the standard procedure, starting from [,-biphenyl]--diazonium tetrafluoroborate ( mg,.00 mmol). After purification, c was isolated as colorless solid ( mg, 0. mmol, %). m.p.: 0- C; H NMR (00 MHz, CDCl ): =.0-. (m, H),.0-. (m, H),.-. ppm (m, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (s, ); C NMR (0 MHz, CDCl ): =.,.,.,.0 (C),. (C),. (C),. (C),., 0. (qt, J(C,) =. Hz, J(C,) =. Hz),. ppm (tq, J(C,) =.0 Hz, J(C,) =. Hz); IR (neat): = 0,,, 00, 00, 0,, 0, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = 0 [M + ] (00), 0 (), (), (), (); HRM (EI-T) calcd. for C H : 0.0; found: 0.0. ynthesis of -phenoxy--[(pentafluoroethyl)thio]benzene (d). Compound d was prepared following the standard procedure, starting from - phenoxybenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, d was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.0 (d, J =. Hz, H),. (t, J =.0 Hz, H),. (t, J =. Hz, H),.0 (d, J =. Hz, H),.0 ppm (d, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): = 0.,.,.0 (C), 0. (C),., 0. (C), 0.0 (tq, J(C,) =. Hz, J(C,) =. Hz),. (C),. (qt, J(C,) =. Hz, J(C,) = 0. Hz),. ppm (t, J(C,) =. Hz); IR (neat): = 0,,,,, 00, 0,,,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = 0 [M + ] (), 0 (00), (), (); HRM (EI-T) calcd. for C H : 0.0; found: 0.0. ynthesis of -bromo--[(pentafluoroethyl)thio]-benzene [CA No.: -- ] (e). Compound e was prepared following the standard procedure, starting from -bromobenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, e was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.-. ppm (m, H); NMR ( MHz, CDCl ): =. (t,

J =. Hz, ),.0 ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =. (C),. (C),.,. (t, J(C,) =. Hz), 0.0 (qt, J(C,) =. Hz, J(C,) = 0. Hz),. ppm (tq, J(C,) =. Hz, J(C,) =. Hz); IR (neat): = 0,,,,, 0, 0, 0,,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = 0 [M + ] (00), (), (), 0 (); HRM (EI-T) calcd. for C H Br: 0.; found: 0.. ynthesis of -fluoro--[(pentafluoroethyl)thio]-benzene [CA No.: 0--] (f). [] Compound f was prepared following the standard procedure, starting from - fluorodiazonium tetrafluoroborate (0 mg, 0.0 mmol). After the reaction, trifluoroethanol as internal standard (.0 µl, 0.0 mmol) was added to the reaction mixture and the pentafluoroethylthiolated product f was formed in % yield as determined by NMR spectroscopic analysis and confirmed by GC-M analytics. NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); M (Ion trap, EI, 0 ev): m/z (%) =. [M + ] (00),.0 (),.0 (),.0 (),.0 (),. (),.0 (). ynthesis of -chloro--[(pentafluoroethyl)thio]-benzene [CA No.: -- ] (g). Compound g was prepared following the standard procedure, starting from -chlorobenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, g was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =. (d, J =. Hz, H),. ppm (d, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),.0 ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =. (C),.0,. (C),. (t, J(C,) =. Hz), 0. (qt, J(C,) =. Hz, J(C,) = 0. Hz),. ppm (tq, J(C,) =.0 Hz, J(C,) =. Hz); IR (neat): = 0,,,,,, 0, 0,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (00), (), (), 0 (); HRM (EI-T) calcd. for C H Cl:.; found:.. ynthesis of -[(pentafluoroethyl)thio]acetophenone [CA No.: --] (h). Compound h was prepared following the standard procedure, starting from - acetylbenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, h was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =. (d, J =.0 Hz, H),. (d, J =.0 Hz, H),. ppm (s, H); NMR

( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.0,.,. (C),. (C),. (t, J(C,) =. Hz), 0. (qt, J(C,) =. Hz, J(C,) = 0. Hz),. (tq, J(C,) =. Hz, J(C,) =. Hz),. ppm; IR (neat): = 0,, 0,, 0, 0,,, 0 cm - ; M (Ion trap, EI, 0 ev): m/z (%) = 0 [M + ] (), (00), (); HRM (EI-T) calcd. for C 0 H : 0.0; found: 0.0. ynthesis of -[(pentafluoroethyl)thio]benzophenone (i). Compound i was prepared following the standard procedure, starting from - benzoylbenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, i was isolated as colorless solid (0 mg, 0. mmol, %). m.p.: - C; H NMR (00 MHz, CDCl ): =.-. (m, H),. (t, J =. Hz, H),. ppm (t, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,.,.,.0, 0., 0.,.,. (t, J(C,) =. Hz), 0.0 (qt, J(C,) =. Hz, J(C,) =.0 Hz),. ppm (tq, J(C,) =. Hz, J(C,) =. Hz); IR (neat): =, 0,,, 0,, 0,, 0,, 0, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (00), (), 0 (); HRM (EI-T) calcd. for C H :.0; found:.0. ynthesis of methyl--[(pentafluoroethyl)thio]benzoate (j). Compound j was prepared following the standard procedure, starting from - (methoxycarbonyl)benzenediazonium tetrafluoroborate (0 mg,.00 mmol). After purification, j was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.0 (d, J =. Hz, H),. (d, J =.0 Hz, H),. ppm (s, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.0,. (C),., 0. (C),. (t, J(C,) =. Hz), 0.0 (qt, J(C,) =. Hz, J(C,) = 0. Hz),. (tq, J(C,) =. Hz, J(C,) =. Hz),. ppm; IR (neat): =,,,,, 0,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), (00), (), 0 (); HRM (EI-T) calcd. for C 0 H :.00; found:.00.

ynthesis of N,N-dimethyl--[(pentafluoroethyl)thio]benzenamine (k). Compound k was prepared following the standard procedure, starting from - (dimethylamino)benzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, k was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.-.0 (m, H),.-. (m, H),.0 ppm (s, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,. (C), 0. (qt, J(C,) =. Hz, J(C,) =. Hz), 0.0 (tq, J(C,) =. Hz, J(C,) =. Hz),. (C), 0. (t, J(C,) =. Hz),. (C) ppm; IR (neat): =,, 0,,,,, 0,, 0, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), (), (), (00), 0 (), 0 (0), (), (0); HRM (EI-T) calcd. for C 0 H 0 N:.0; found:.00. ynthesis of N-[-[(pentafluoroethyl)thio]phenyl]acetamide (l). Compound l was prepared following the standard procedure, starting from - (acetylamino)benzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, l was isolated as slightly yellow solid ( mg, 0. mmol, %). m.p.: - C; H NMR (00 MHz, CDCl ): =.0 (s, H),. ppm (s, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,. (C),. (C),. (qt, J(C,) =. Hz, J(C,) = 0. Hz), 0. (tq, J(C,) =. Hz, J(C,) =. Hz),. (t, J(C,) =. Hz),. ppm; IR (neat): =, 0,,,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (0), (), (00); HRM (EI-T) calcd. for C 0 H N :.0; found:.0. ynthesis of -[(pentafluoroethyl)thio]nitrobenzene (m). Compound m was prepared following the standard procedure, starting from -nitrobenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, m was isolated as slightly yellow oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =. (d, J =. Hz, H),. ppm (d, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ), 0. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,. (C), 0. (t, J(C,) =. Hz),. (C), 0.0 (qt, J(C,) = 0. Hz, J(C,) =. Hz),. ppm (tq, J(C,) =. Hz,

J(C,) =.0 Hz); IR (neat): =, 00,, 0,,, 0, 0,,, 0,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), (), 0 (), (00), 0 (0), (), 0 (); HRM (EI-T) calcd. for C H N :.; found:.. ynthesis of -[(pentafluoroethyl)thio]benzonitrile (n). Compound n was prepared following the standard procedure, starting from -cyanobenzenediazonium tetrafluoroborate ( mg,.00 mmol). After purification, n was isolated as colorless solid (0 mg, 0. mmol, %). m.p.: - C; H NMR (00 MHz, CDCl ): =. (d, J =. Hz, H),. ppm (d, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),.0 ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =. (C),. (C),. (t, J(C,) =. Hz), 0.0 (qt, J(C,) = 0. Hz, J(C,) = 0. Hz),. (tq, J(C,) =.0 Hz, J(C,) =. Hz),.,.0 ppm; IR (neat): = 0, 0,,,, 0, 0,,, 0, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (00), (), (), 0 (), 0 (); HRM (EI-T) calcd. for C H N :.; found:.. ynthesis of -[(pentafluoroethyl)thio]quinoline (o). Compound o was prepared following the standard procedure, starting from quinoline--diazonium tetrafluoroborate ( mg,.00 mmol). After purification, o was isolated as colorless solid ( mg, 0. mmol, %). m.p.: - C; H NMR (00 MHz, CDCl ): =.00 (s, H),. (s, H),. (d, J =. Hz, H),.-. (m, H),. ppm (t, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,.,.,.,.0,.,., 0. (qt, J(C,) =. Hz, J(C,) = 0. Hz),. (tq, J(C,) =. Hz, J(C,) =. Hz),. ppm (t, J(C,) =. Hz); IR (neat): = 0,,,,,,, 00,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), 0 (00), (), (); HRM (EI-T) calcd. for C H N :.0; found:.0. ynthesis of -[(pentafluoroethyl)thio]quinoline (p). Compound p was prepared following the standard procedure, starting from quinoline--diazonium tetrafluoroborate ( mg,.00 mmol). After purification, p was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.0 (dd, J =., 0

. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. ppm (dd, J =.,. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,.,.,., 0.,.,.,. (t, J(C,) =. Hz), 0. (qt, J(C,) =.0 Hz, J(C,) = 0. Hz),. ppm (tq, J(C,) =. Hz, J(C,) =. Hz); IR (neat): = 0,,,, 0, 0,,,,, 0 cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), 0 (00), (); HRM (EI-T) calcd. for C H N :.0; found:.00. ynthesis of -[(pentafluoroethyl)thio]quinoline (q). Compound q was prepared following the standard procedure, starting from quinoline--diazonium tetrafluoroborate ( mg,.00 mmol). After purification, q was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =.0 (dd, J =.,. Hz, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (dd, J =.0,. Hz, H),. (t, J =. Hz, H),.0 ppm (dd, J =.,. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),.0 ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,.,., 0., 0.0,.,.,.0, 0. (qt, J(C,) = 0. Hz, J(C,) = 0. Hz),. ppm (tq, J(C,) =. Hz, J(C,) =. Hz); IR (neat): = 0,,,, 0, 0, 0,,, 0, 0 cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (0), 0 (00), (); HRM (EI-T) calcd. for C H N :.0; found:.0. ynthesis of -ethyl--[(pentafluoroethyl)thio]-h-carbazole (r). Compound r was prepared following the standard procedure, starting from -ethyl-h-carbazol-- diazonium tetrafluoroborate (0 mg,.00 mmol). After purification, r was isolated as colorless solid ( mg, 0. mmol, %). m.p.: - C; H NMR (00 MHz, CDCl ): =.0 (s, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (dt, J =.,. Hz, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (q, J =. Hz, H),. ppm (t, J =. Hz, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =., 0.,., 0.,.,.,., 0., 0. (qt, J(C,) =. Hz, J(C,) = 0.0 Hz),.,. (tq, J(C,) =.0 Hz,

J(C,) =. Hz), 0. (t, J(C,) =. Hz), 0., 0.,.,. ppm; IR (neat): = 0,,,, 0, 00, 0,,,,, cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), 0 (), (00), (), (), (); HRM (EI-T) calcd. for C H N :.0; found:.0. ynthesis of methyl--[(pentafluoroethyl)thio]thiophene--carboxylate (s). Compound s was prepared following the standard procedure, starting from - (methoxycarbonyl)thiophene--diazonium tetrafluoroborate ( mg,.00 mmol). After purification, s was isolated as colorless oil ( mg, 0. mmol, %). H NMR (00 MHz, CDCl ): =. (d, J =. Hz, H),.0 (d, J =. Hz, H),. ppm (s, H); NMR ( MHz, CDCl ): =. (t, J =. Hz, ),. ppm (q, J =. Hz, ); C NMR (0 MHz, CDCl ): =.,.,. (t, J(C,) =. Hz),.0,. (t, J(C,) =. Hz), 0. (qt, J(C,) =. Hz, J(C,) =. Hz),. (tq, J(C,) =.0 Hz, J(C,) =. Hz),. ppm; IR (neat): =, 0, 0,,, 0, 0,,,,, 0 cm - ; M (Ion trap, EI, 0 ev): m/z (%) = [M + ] (), (), (00), (), (0); HRM (EI-T) calcd. for C H :.; found:..

pectroscopic data 00.EP CHLRRM-d 0 CH...... a.0.0.0..0..0..0..0..0..0..0..0 0. 0.EP -. 0 CH.0 0. 0. a 0. Normalized Intensity 0. 0. 0. 0. 0. -. -. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

0.esp. 0 CH a CHLRRM-d...00..0...... 0. 0. 0....0.....0.0.00.. 00 0 0 0 0 00 0 0 0 0 0 0.esp. CH 0 a.0...0.. 0. 0.....0.0....0..... 0...0..0..0 0. 0.0..0..0..0..0..0..0..0.

.esp....... CHLRRM-d. b CH 0.0.0.0..0..0..0..0..0..0..0..0 0. 0.0 0.esp -. 0. 0. b CH 0 0. Normalized Intensity 0. 0. 0. 0. -.0 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

.esp.. b CH 0.0.....0.... 0. 0. 0. 0.0 0.0............0.. CHLRRM-d.00.. 00 0 0 0 0 00 0 0 0 0 0.esp. b CH 0....0 0. 0. 0.0............0. 0.0.. 0......0..0..0 0. 0.0..0..0..0..0..0..0

.esp CHLRRM-d 0....0.0...... c 0.0.0.0..0..0..0..0..0..0..0..0 0. 0.0 0. 0..esp -. c 0 0 0. Normalized Intensity 0. 0. 0. 0. -. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

CNMR BIPHENYL.EP.0 0.0 c 0.0...0......... 0. 0. 0. 0. 0.0...0.....0....0.00. CHLRRM-d. CNMR BIPHENYL.EP 00 0 0 0 0 00 0 0 0 0 0. 0 c 0....... 0. 0....0....0....0 0. 0. 0.0...0..0..0..0 0. 0.0..0..0..0..0..0..0.

.esp CHLRRM-d 0.........0.0.0.00 0 d.0.0.0..0..0..0..0..0..0..0..0..0 0. 0.0.esp -. -. 0 0. 0. d 0 Normalized Intensity 0. 0. 0. 0. -. 0. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

0.esp 0. 0. 0.....0..0 0.0.... d 0 0.0.00. CHLRRM-d.. 0........... 00 0 0 0 0 00 0 0 0 0 0 0.esp.0 0.. 0 0 d..0.0... 0. 0. 0................ 0 0

000.esp CHLRRM-d........ 0 e Br.0..0..0..0..0..0..0..0..0 0. 0 0.esp -..0 0. -. -. 0 0. e Br 0. Normalized Intensity 0. 0. 0. 0. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

.esp. 0 e Br.....0...0 0. 0.....0......0.00. CHLRRM-d. 00 0 0 0 0 00 0 0 0 0 0.esp.0 0 e Br....0.. 0. 0...........0.. 0. 0...0..0..0..0 0. 0.0..0..0..0..0..0..0.

.esp CHLRRM-d 0....0. g Cl.0.0..0..0..0..0..0..0..0..0 0. 0.0 0. 0. 0.esp -. g Cl 0 Normalized Intensity 0. 0. 0. 0. 0. -. -. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

.esp. 0 g Cl.00....0..... 0. 0. 0.0...0.......0.00.. CHLRRM-d 00 0 0 0 0 00 0 0 0 0 0.esp 0 g. Cl...0. 0. 0......0.......0.. 0. 0.0.....0..0..0 0. 0.0..0..0..0..0..0..0.

0.esp CHLRRM-d C H 0.00.00......... h.0.0.0.0..0..0..0..0..0..0..0..0 0. 0.esp -. H C 0 0. 0. h 0. Normalized Intensity 0. 0. 0. 0. -. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

.esp. H C 0..00 CHLRRM-d h....0............. 00 0 0 0 0 00 0 0 0 0 0.esp H C 0 h....... 0....0..0.00.... 0. 0. 0.00....0..0..0..0..0 0. 0.0..0..0..0..0..0..0..0..0.

0.esp CHLRRM-d 0 0.....0......0. i.0.0.0..0..0..0..0..0..0..0..0 0. 0.0 00.esp -. 0 0 0. 0. 0. -.0 i Normalized Intensity 0. 0. 0. 0. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

.esp.0 0.0 0 0 CHLRRM-d..00. i. 0..0......... 0. 0.0 0.0.0.......0.0.0....esp 00 0 0 0 0 00 0 0 0 0 0 0 0 i..... 0. 0. 0.0.. 0.0.0..0.0.0...... 0

.esp CHLRRM-d CH 0.0.0.... j.0.0.0.0..0..0..0..0..0..0..0..0 0. 0.esp -. CH 0 0. 0. -. j 0. Normalized Intensity 0. 0. 0. 0. 0. 0. 0.0. 0 0-0 -0-0 -0-00 -0-0 -0-0 -00-0

0.esp 0.. CH 0...00.. j.00.0..0..... 0. 0. 0............... 00 0 0 0 0 00 0 0 0 0 0 0.esp CH 0 j..0..... 0. 0... 0............. 0 0 0 0

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.esp CHLRRM-d H C 0 s.00.....0....0....0 0. 0...0...0....0.esp 00 0 0 0 0 00 0 0 0 0 0.0 H C 0 s.....0.....0 0...0....0....0 0. 0. 0 N. V. Kondratenko, V. I. Popov, A. A. Kolomeitsev, E. P. aenko, V. V. Prezhdo, A. E. Lutskii, L. M. Yagupol'skii Zhurnal rganicheskoi Khimii 0, V().