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Volumn 72, Issue 13, 2007, Pages 4932-4935

Formation of diethyl 2-amino-1-cyclopentenylphosphonates: A simple synthesis with a unique mechanism

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CYCLIZATION; PROTON TRANSFER;

EID: 84961978627     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070535b     Document Type: Article
Times cited : (11)

References (27)
  • 1
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    • Some recent references are: (a) Palacios, F.; de Retana, A. M. O.; Pascual, S.; Oyarzabal, J. J. Org. Chem. 2004, 69, 8767-8774.
    • Some recent references are: (a) Palacios, F.; de Retana, A. M. O.; Pascual, S.; Oyarzabal, J. J. Org. Chem. 2004, 69, 8767-8774.
  • 4
    • 17244379375 scopus 로고    scopus 로고
    • Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899-932.
    • Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899-932.
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    • 0002815779 scopus 로고    scopus 로고
    • Some recent references: (a) Quntar, A. A.; Srebnik, M. Org. Lett. 2001, 3, 1379.
    • Some recent references: (a) Quntar, A. A.; Srebnik, M. Org. Lett. 2001, 3, 1379.
  • 21
    • 84962465656 scopus 로고    scopus 로고
    • In the special case of a protic environment such as methylamine in water or ethanolamine, it is expected that protonation of the carbanion should be rapid. However, as indicated by calculations (unpublished) this step is reversible. Therefore, the direct cyclization of the carbanion, which leads to a very stable compound, serves as the driving force for the reaction and pushes the system toward its thermodynamically stable product.
    • In the special case of a protic environment such as methylamine in water or ethanolamine, it is expected that protonation of the carbanion should be rapid. However, as indicated by calculations (unpublished) this step is reversible. Therefore, the direct cyclization of the carbanion, which leads to a very stable compound, serves as the driving force for the reaction and pushes the system toward its thermodynamically stable product.
  • 23
    • 84962451669 scopus 로고    scopus 로고
    • Note that we did not investigate the corresponding 5-iodo and 5-bromo alkynylphosphonates since Ma has already demonstrated that 5-iodo-1- alkynylphosphonate reacts with amines to give azaheterocycles, presumably by an initial SN2 attack on the C-I bond. In addition it is known that bromides are intermediate in their activity between iodides and chlorides. Thus, we believe that their investigation would not provide any additional insight to the mechanistic interpretation
    • N2 attack on the C-I bond. In addition it is known that bromides are intermediate in their activity between iodides and chlorides. Thus, we believe that their investigation would not provide any additional insight to the mechanistic interpretation.
  • 24
    • 84962451665 scopus 로고    scopus 로고
    • 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, Klene, 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-La
    • 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.; Klene, 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.04; Gaussian, Inc.: Pittsburgh, PA, 2003.


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