Efficient preparation of E-β-iodovinyl phenylsulfone by finkelstein reaction at a vinylic center

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8089-8092

  Zoller, T ^a   Uguen, D ^a   De Cian, A ^a   Fischer, J ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,2 TRICHLOROETHANE; ACETYLENE; BENZENESULFONIC ACID DERIVATIVE; BETA IODOVINYL PHENYLSULFONE; CHLORINE; DIMETHYL SULFOXIDE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE; X RAY ANALYSIS;

EID: 0032578897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01835-8     Document Type: Article

References (11)

1. 1-Russell, G. A.; Ngoviwatchai, P.; Tashtoush, H. I.; Pla-Dalmau, A.; Khanna, R. K. J. Am. Chem. Soc. 1988, 110, 3530-3538.
2. 2-a) Truce, W. E.; Wolf, G. C. J. Chem. Soc. Chem. Commun. 1969, 150;
3. b) Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727-1732.
4. 3b proved not so rewarding, the sulfone E-1b being then isolated in a yield not exceeding 15%;
5. b) Iwata, N.; Morioka, T.; Kobayashi, T.; Asada, T.; Kinoshita, H; Inomata, K. Bull. Chem. Soc. Jpn. 1992, 65, 1379-1388. Physical data (M. p., NMR) consonant with the values we recorded are given for compound E-1b, but no indication is provided concerning either the used protocol or the yield.
6. 4-McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. Tetrahedron Lett. 1985, 26, 6301-6304.
7. 5-a) Pelter, A.; Ward, R.; Litle, G. M. J. Chem. Soc. Perkin I 1990, 2775-2790;
8. b) Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317-4319.
9. 2). The solvents were evaporated and the resulting white solid was recrystallized from diisopropyl ether to afford the pure sulfone E-1a (2.77g; 76%) as colourless crystals (M. p. 77-78 °C).
10. 3. The results presented herein are taken in part from the doctorat dissertation of T. Z. (Strasbourg, 1998).
11. -3. The absolute structure was determined by refining Flack's x parameter. In common: room temperature, Nonius MACH3 diffractometer and MoKα graphite monochromated radiation (λ= 0.71073 Å), step-scan. The structures were solved using direct methods and refined against |F|. Hydrogen atoms were introduced as fixed contributors. Empirical absorption corrections derived from psi scans. For all computations the Nonius OpenMoleN package (OpenMoleN, Interactive Structure Solution, Nonius B.V., Delft, The Nederlands (1997)) was used. Further details of the crystal structure investigation are available on request from the Director of Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 IEW (U.K.), on quoting the full journal citation.