Facile one-pot preparation of 3-chloro-2-(chloromethy)propene and an ab initio study of the deamination reaction of nitrosoaziridine

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6784-6786

  Martinu, Tomas ^a   Dailey, William P ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLORO 2 (CHLOROMETHYL)PROPENE; ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; N NITROSOAZIRIDINE; UNCLASSIFIED DRUG;

ARTICLE; DEAMINATION; HYDROLYSIS; REACTION ANALYSIS; STEREOSPECIFICITY; STOICHIOMETRY; SYNTHESIS;

EID: 0034613354     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000734u     Document Type: Article

References (22)

1. Bumgardner, C. L.; McCallum, K. S.; Freeman, J. P. J. Am. Chem. Soc. 1961, 83, 4417.
2. Clark, R. D.; Helmkamp, G. K. J. Org. Chem. 1964, 29, 1316.
3. Mock, W. L.; Isaac, P. A. H. J. Am. Chem. Soc. 1972, 94, 2749.
4. Rundel, W.; Müller, E. Chem. Ber. 1963, 96, 2528.
5. Carlson, R. M.; Lee, S. Y. Tetrahedron Lett. 1969, 10, 4001.
6. Lee, K.; Kim, Y. H. Synth. Commun. 1999, 29, 1241 and references therein.
7. (a) Semmler, K.; Szeimies, G.; Belzner, J. J. Am. Chem. Soc. 1985, 107, 6410.
8. (b) Lynch, K. M.; Dailey, W. P. J. Org. Chem. 1995, 60, 4666.
9. (c) Lynch, K. M.; Dailey, W. P. Org. Synth. 1998, 75, 89 and references therein.
10. Boikov, Y. A.; Bakhmenko, V. B.; V'yunov, K. A.; Ginak, A. I. J. Org. Chem. USSR 1986, 22, 261.
11. If desired, compounds 1, 3, and 4 can be isolated and purified at the appropriate points of the preparation. See Experimental Section.
12. For a review of the preparation and reactions of sulfinylamines and related compounds, see: Kresze, G.; Wucherpfennig, W. Angew. Chem., Int. Ed. Engl. 1967, 6, 149 and references therein.
13. Hoffmann, R.; Woodward, R. B. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
14. Gaussian 94, Revision E.2, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc., Pittsburgh, PA, 1995.
15. Curtiss, L. A.; Ragavachari, K.; Pople, J. A. J. Chem. Phys. 1993, 98, 1293.
16. Shustov, G. V.; Kachanov, A. V.; Kadorkina, G. K.; Kostyanovsky, R. G.; Rauk, A. J. Am. Chem. Soc. 1992, 114, 8257.
17. -1.
18. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1978; pp 23-32.
19. If the reaction is scaled down to 25 g of TRIS, the heating time may be reduced to 3 h.
20. 6): δ 59.11, 44.33; MS (CI) 176.0 (M - Cl).
21. 2N.
22. 3): δ 135.06, 122.49, 43.77, 38.28. Formation of trichloropropene under the employed reaction conditions is precedented by Boikov, Yu. A.; V'yunov, K. A.; Ginak, A. I. J. Org. Chem. USSR 1982, 18, 2010.