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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 However, as indicated by calculations (unpublished) this step is reversible.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.
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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 However, as indicated by calculations (unpublished) this step is reversible.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.
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Structural Theory of Organic Chemistry
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23
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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
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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.
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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
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