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Volumn 9, Issue 12, 2007, Pages 2409-2412

A new route to the synthesis of (E)-and (Z)-2-alkene-4-ynoates and nitriles from vic-diiodo-(E)-alkenes catalyzed by Pd(0) nanoparticles in water

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; NANOPARTICLE; NITRILE; PALLADIUM; WATER;

EID: 34250893788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0708121     Document Type: Article
Times cited : (54)

References (23)
  • 3
    • 0004294109 scopus 로고
    • Viehe, H. G, Ed, Mercel Dekker: New York
    • (c) Bohlmann, F.; Chemistry of Acetylenes: Viehe, H. G., Ed.; Mercel Dekker: New York, 1969, p 977.
    • (1969) Chemistry of Acetylenes , pp. 977
    • Bohlmann, F.1
  • 19
    • 34250830513 scopus 로고    scopus 로고
    • Representative Experimental Procedure for Enyne Synthesis (entry 4, Table 2, To a stirred mixture of tetrabutylammonium bromide (323 mg, 1 mmol) and PdCl2 (3.5 mg, 0.02 mmol) in water (3 mL) were added 1-(1,2-diiodovinyl)-4-methylbenzene (370 mg, 1 mmol, methyl acrylate (344 mg, 4 mmol; excess amount was used to avoid any loss during reflux, and Na 2CO3 (424 mg, 4 mmol, The mixture was then heated at 80 °C (oil bath) for 6 h (TLC, After being cooled the reaction mixture was. extracted with Et2O (3 × 10 mL, The ether extract was washed with water and brine and dried (Na2SO4, The solvent was evaporated under reduced pressure to leave a crude product that was purified by column chromatography over silica gel (ether-hexane 5:95) to afford the pure product, 5-ptolylpent-2-en-4-ynoic acid methyl ester (156 mg, 78, as a yellow solid: mp 72-73 °C; IR (KBr) 2852, 2193, 1718, 1622 cm-1;
    • 2: C, 77.98: H, 6.04. Found: C, 77.88; H, 5.99. The combined aqueous layer and extract was concentrated under reduced pressure and was used for the next reaction.
  • 23
    • 34250836050 scopus 로고    scopus 로고
    • The ground state structural calculations for the intermediate products such as cis and trans ester were computed by using Hartee-Fock (HF/ STo-3G) levels with GAUSSIAN software: Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Kiene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Fore
    • The ground state structural calculations for the intermediate products such as cis and trans ester were computed by using Hartee-Fock (HF/ STo-3G) levels with GAUSSIAN software: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.