Controlling Selectivity by Controlling the Path of Trajectories

Journal of the American Chemical Society

Volumn 137, Issue 45, 2015, Pages 14244-14247

  Biswas, Bibaswan ^a   Singleton, Daniel A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

AMMONIUM YLIDES; COMPUTATIONAL DYNAMICS; CROSSOVER EXPERIMENTS; DYNAMIC TRAJECTORIES; KINETIC ISOTOPE EFFECTS; REACTION CONDITIONS; SIGMATROPIC REARRANGEMENTS; TRANSITION STATE;

TRAJECTORIES;

AMMONIA; AMMONIUM YLIDE; ISOTOPE; METHANOL; UNCLASSIFIED DRUG; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HYDROGEN BOND; STEVENS SOMMELET HAUSER REARRANGEMENT; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; SYNTHESIS; THERMODYNAMICS;

HYDROGEN BONDING; KINETICS; METHANOL; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; THERMODYNAMICS;

EID: 84947968131     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b08635     Document Type: Article

References (28)

1. Biswas, B.; Collins, S. C.; Singleton, D. A. J. Am. Chem. Soc. 2014, 136, 3740-3743 10.1021/ja4128289
2. Hauser, C. R.; Kantor, S. W.; Brasen, W. R. J. Am. Chem. Soc. 1953, 75, 2660-2663 10.1021/ja01107a032
3. Schöllkopf, U.; Fellenberger, K. Annalen 1966, 698, 80-85 10.1002/jlac.19666980107
4. Millard, B. J.; Stevens, T. S. J. Chem. Soc. 1963, 3397-3403 10.1039/jr9630003397
5. Baldwin, J. E.; Hackler, R. E. J. Am. Chem. Soc. 1969, 91, 3646-3647 10.1021/ja01041a038
6. Rautenstrauch, V. J. Chem. Soc. D 1970, 4-6 10.1039/c29700000004
7. Baldwin, J. E.; Brown, J. E.; Cordell, R. W. J. Chem. Soc. D 1970, 31-32 10.1039/c29700000031
8. Chantrapromma, K.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1977, 97-99 10.1039/c39770000097
9. Chantrapromma, K.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1983, 1029-1039 10.1039/p19830001029
10. Jemison, T. L.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1458-1461 10.1039/p19800001458
11. Tayama, E.; Takedachi, K.; Iwamoto, H.; Hasegawa, E. Tetrahedron 2010, 66, 9389-9395 10.1016/j.tet.2010.09.105
12. Tayama, E.; Kimura, H. Angew. Chem., Int. Ed. 2007, 46, 8869-8871 10.1002/anie.200703832
13. Yamamoto, Y.; Oda, J.; Inouye, Y. Tetrahedron Lett. 1979, 20, 2411-2414 10.1016/S0040-4039(01)86306-1
14. Hayashi, Y.; Oda, R. Tetrahedron Lett. 1968, 9, 5381-5384 10.1016/S0040-4039(00)75389-5
15. Pine, S. H.; Munemo, E. M.; Phillips, T. R.; Bartolini, G.; Cotton, W. D.; Andrews, G. C. J. Org. Chem. 1971, 36, 984-991 10.1021/jo00806a028
16. Tanaka, T.; Shirai, N.; Sugimori, J.; Sato, Y. J. Org. Chem. 1992, 57, 5034-5036 10.1021/jo00044a050
17. Narita, K.; Shirai, N.; Sato, Y. J. Org. Chem. 1997, 62, 2544-2549 10.1021/jo962226j
18. Kocharyan, S. T.; Karapatyan, V. E.; Razina, T. L.; Babyan, A. T. Russ. J. Gen. Chem. 1990, 18, 2277-2282
19. Thomas, J. R.; Waas, J. R.; Harmata, M.; Singleton, D. A. J. Am. Chem. Soc. 2008, 130, 14544-14555 10.1021/ja802577v
20. Wang, Z.; Hirschi, J. S.; Singleton, D. A. Angew. Chem., Int. Ed. 2009, 48, 9156-9159 10.1002/anie.200903293
21. Kelly, K. K.; Hirschi, J. S.; Singleton, D. A. J. Am. Chem. Soc. 2009, 131, 8382-8383 10.1021/ja9031083
22. Gonzalez-James, O. M.; Kwan, E. E.; Singleton, D. A. J. Am. Chem. Soc. 2012, 134, 1914-1917 10.1021/ja208779k
23. Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336-6344 10.1021/ja00128a024
24. Singleton, D. A.; Szymanski, M. J. J. Am. Chem. Soc. 1999, 121, 9455-9456 10.1021/ja992016z
25. Singleton, D. A.; Schulmeier, B. E. J. Am. Chem. Soc. 1999, 121, 9313-9317 10.1021/ja9919229
26. Gonzalez-James, O. M.; Zhang, X.; Datta, A.; Hrovat, D. A.; Borden, W. T.; Singleton, D. A. J. Am. Chem. Soc. 2010, 132, 12548-12549 10.1021/ja1055593
27. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167 10.1021/ar700111a
28. Hase, W. L.; Song, K. H.; Gordon, M. S. Comput. Sci. Eng. 2003, 5, 36-44 10.1109/MCISE.2003.1208640