摘要:

Synthesis and X-Ray Crystal Structure of 1,2-Dichloro-1,2-bis(phenyltellanyl)ethylene Georges Le Guillanton,*a Alexander V. Martynov,a Jacques Delaunay,b Nicolas Mercierb and AmeÈÍ deÈÍ e Rioub aLaboratoire de Synthe se et EÈÍ lectrochimie Organiques UniversiteÈÍ Catholique de l'Quest BP 808 49008 ANGERS Cedex 01 France bLaboratoire d'IngeÈÍ nierie MoleÈÍ culaire et MateÈÍ riaux Organiques (UMR CNRS no 6501) UniversiteÈÍ d'Angers 2 Boulevard Lavoisier 49045 ANGERS Cedex France 1,2-Dichloro-1,2-bis(phenyltellanyl)ethylene 1a prepared by ditelluration of dichloroacetylene 3 with diphenyl ditelluride exists in the trans-form as confirmed by X-ray structure analysis. 1,2-Dichloro-1,2-bis(phenyltellanyl)ethylene 1a has been prepared by the general method of ditelluration of dichloro- acetylene 3 with diphenyl ditelluride 5.7 We found that the main product formed in this reaction obtained in 91% yield was a crystalline solid with mp 152 8C but not the one with mp 82 8C as already mentioned.7 The IR NMR (1H 13C) spectra and elemental analysis of this compound corresponded to the proposed structure Ph¡ÓTe¡ÓC(Cl).C(Cl)¡ÓTe¡ÓPh 1a.In particular in the IR spectrum there were no bands corresponding to Te¡ÓO bonding. 13C NMR chemical shifts were assigned by heteronuclear multiple bond correlation (HMBC experiment) according to Scheme 3 (Table 1) (see full text for both). 13C NMR assignments are in good agreement with those reported for Ph¡ÓX¡ÓCH.CH2 (X O S Se and Te) in a previous work.8 Carbon C1 does not present any correlation spot. trans-Conguration with a symmetry centre in the middle of the C14H10Cl2Te2 molecule is found from an X-ray study for the 1,2-dichloro-1,2-bis(phenyltellanyl)ethylene molecule 1a (Fig.1). In the studied molecule atoms C(2) Te C(1) Cl C(1) Cl Te and C(2) lie approximately in one plane and the C¡ÓTe¡ÓC angle of 96.48 is close to that found for C¡ÓSe¡ÓC (998). The C¡ÓCl distances are well dened [1.723(7) A ] and in good agreement with the standard values while the Te¡ÓC distances are also well dened and vary between 2.125(7) and 2.105(9) A . Crystal Data for 1,2-Dichloro-bis( phenyltellanyl )ethylene 1a.Triclinic space group P1 a 5.897(3) b 7.951(2) c 8.896(3) A 111.66(2) 94.97(3) 92.16(3)8 V 385.1(3) A 3 Z 1 Dc=2.17 g cm£¾3 R 0.064 Rw 0.092. The structure of C14H10Cl2Te2 1a was studied by single crystal X-ray diraction. The crystal was selected by optical examination and X-ray diraction data were collected at room temperature on an Enraf Nonius MACH3 diracto- meter with graphite monochromated MoKa radiation.A crystal cell was obtained from 25 reections randomly found in the 10¡Ó168 y range. The conditions of intensity measurement are reported in Table 2 (see full text). 1241 independent observed reections corrected from Lorentz- polarization eects were available for renements. The scat- tering factors for all atoms were taken from International tables of crystallography.9 The structure was rst solved by direct methods (SIR10) with the program MolEN,11 and rened after absorption correction (empirical method *To receive any correspondence. J. CHEM. RESEARCH (S) 1998 681 J. Chem. Research (S) 1998 681 J.Chem. Research (M) 1998 3001¡Ó3010 Fig. 1 ORTEP13 view of the C14H10Cl2Te2 molecule difabs option12 of MolEN) by full matrix least-squares methods using MolEN. After the last renement the nal residual (R) factor was 6.4% (Rw 9.2%). This study was supported partly by the grant 166868D of Ministe re des Aaires Etrange res. Techniques used 1H and 13C NMR IR UV X-Ray diraction elemental analysis References 14 Table 1 NMR data and heteronuclear multiple bond correlation Table 2 Crystallographic data and conditions of data collection for C14H10Cl2Te2 Table 3 Positional parameters and their estimated standard deviations Table 4 Bond distances (A ) and angles (deg) Table 5 Table of general displacement parameter expressions Received 19th June 1998; Accepted 3rd August 1998 Paper E/8/04668J References cited in this synopsis 7 A.V. Martynov and A. N. Mirskova Zh. Org. Khim. 1995 31 872. 8 G. A. Kalabin V. M. Bzhezovskii D. F. Kushnarev and A. G. Proidakov Zh. Org. Khim. 1981 17 1143. 9 International Tables for X-Ray Crystallography Kynoch Press Birmingham England vol. IV 1974. G. Polidori R. Spagna and D. Viterbo SIR. J. Appl. Crystallogr. 10 M. C. Burla M. Camalli G. Cascarano C. Giacovazzo 1989 22 389. 11 C. K. Fair in MolEN An Interactive Intelligent System for Crystal Structure Analysis User Manual Enraf¡ÓNonius Delft 12 N. Walker and D. Stuart Acta Crystallogr. Sect. A 1983 39 The Netherlands 1990. 158. 13 C. K. Johnson. ORTEP. Report ORNL-5138 Oak Ridge National Laboratory Tennessee USA 1976. Synthesis and X-Ray Crystal Structure of1,2-Dichloro-1,2-bis(phenyltellanyl)ethyleneGeorges Le Guillanton,*a Alexander V.Martynov,aJacques Delaunay,b Nicolas Mercierb and AmeÈÍ deÈÍ e RioubaLaboratoire de Synthe se et EÈÍ lectrochimie Organiques UniversiteÈÍ Catholique de l'Quest BP 808,49008 ANGERS Cedex 01 FrancebLaboratoire d'IngeÈÍ nierie MoleÈÍ culaire et MateÈÍ riaux Organiques (UMR CNRS no 6501),UniversiteÈÍ d'Angers 2 Boulevard Lavoisier 49045 ANGERS Cedex France1,2-Dichloro-1,2-bis(phenyltellanyl)ethylene 1a prepared by ditelluration of dichloroacetylene 3 with diphenylditelluride exists in the trans-form as confirmed by X-ray structure analysis.1,2-Dichloro-1,2-bis(phenyltellanyl)ethylene 1a has beenprepared by the general method of ditelluration of dichloro-acetylene 3 with diphenyl ditelluride 5.7We found that the main product formed in this reaction,obtained in 91% yield was a crystalline solid with mp152 8C but not the one with mp 82 8C as alreadymentioned.7 The IR NMR (1H 13C) spectra and elementalanalysis of this compound corresponded to the proposedstructure Ph¡ÓTe¡ÓC(Cl).C(Cl)¡ÓTe¡ÓPh 1a.In particular inthe IR spectrum there were no bands corresponding toTe¡ÓO bonding.13C NMR chemical shifts were assigned by heteronuclearmultiple bond correlation (HMBC experiment) accordingto Scheme 3 (Table 1) (see full text for both). 13C NMRassignments are in good agreement with those reported forPh¡ÓX¡ÓCH.CH2 (X O S Se and Te) in a previous work.8Carbon C1 does not present any correlation spot.trans-Conguration with a symmetry centre in the middleof the C14H10Cl2Te2 molecule is found from an X-ray studyfor the 1,2-dichloro-1,2-bis(phenyltellanyl)ethylene molecule1a (Fig.1). In the studied molecule atoms C(2) Te C(1),Cl C(1) Cl Te and C(2) lie approximately in one planeand the C¡ÓTe¡ÓC angle of 96.48 is close to that foundfor C¡ÓSe¡ÓC (998). The C¡ÓCl distances are well dened[1.723(7) A ] and in good agreement with the standardvalues while the Te¡ÓC distances are also well dened andvary between 2.125(7) and 2.105(9) A .Crystal Data for 1,2-Dichloro-bis( phenyltellanyl )ethylene1a.Triclinic space group P1 a 5.897(3) b 7.951(2),c 8.896(3) A 111.66(2) 94.97(3) 92.16(3)8,V 385.1(3) A 3 Z 1 Dc=2.17 g cm£¾3 R 0.064 Rw 0.092.The structure of C14H10Cl2Te2 1a was studied by singlecrystal X-ray diraction. The crystal was selected by opticalexamination and X-ray diraction data were collected atroom temperature on an Enraf Nonius MACH3 diracto-meter with graphite monochromated MoKa radiation.Acrystal cell was obtained from 25 reections randomlyfound in the 10¡Ó168 y range. The conditions of intensitymeasurement are reported in Table 2 (see full text). 1241independent observed reections corrected from Lorentz-polarization eects were available for renements. The scat-tering factors for all atoms were taken from Internationaltables of crystallography.9 The structure was rst solved bydirect methods (SIR10) with the program MolEN,11 andrened after absorption correction (empirical method,difabs option12 of MolEN) by full matrix least-squaresmethods using MolEN. After the last renement the nalresidual (R) factor was 6.4% (Rw 9.2%).This study was supported partly by the grant 166868Dof Ministe re des Aaires Etrange res.Techniques used 1H and 13C NMR IR UV X-Ray diraction,elemental analysisReferences 14Table 1 NMR data and heteronuclear multiple bond correlationTable 2 Crystallographic data and conditions of data collection forC14H10Cl2Te2Table 3 Positional parameters and their estimated standarddeviationsTable 4 Bond distances (A ) and angles (deg)Table 5 Table of general displacement parameter expressionsReceived 19th June 1998; Accepted 3rd August 1998Paper E/8/04668JReferences cited in this synopsis7 A.V. Martynov and A. N. Mirskova Zh. Org. Khim. 1995 31,872.8 G. A. Kalabin V. M. Bzhezovskii D. F. Kushnarev and A. G.Proidakov Zh. Org. Khim. 1981 17 1143.9 International Tables for X-Ray Crystallography Kynoch Press,Birmingham England vol. IV 1974.10 M. C. Burla M. Camalli G. Cascarano C. Giacovazzo,G. Polidori R. Spagna and D. Viterbo SIR. J. Appl. Crystallogr.,1989 22 389.11 C. K. Fair in MolEN An Interactive Intelligent System forCrystal Structure Analysis User Manual Enraf¡ÓNonius Delft,The Netherlands 1990.12 N. Walker and D. Stuart Acta Crystallogr. Sect. A 1983 39,158.13 C. K. Johnson. ORTEP. Report ORNL-5138 Oak RidgeNational Laboratory Tennessee USA 1976.J. Chem. Research (S),1998 681J. Chem. Research (M),1998 3001¡Ó3010Fig. 1 ORTEP13 view of the C14H10Cl2Te2 molecule*To receive any correspondence.J. CHEM. RESEARCH (S) 1998 681

ISSN:0308-2342    

DOI:10.1039/a804668i

出版商:RSC    

年代:1998

数据来源: RSC