Acetyl chloride-ethanol brings about a remarkably efficient conversion of allyl acetates into allyl chlorides

Tetrahedron

Volumn 59, Issue 46, 2003, Pages 9111-9116

  Yadav, Veejendra K ^a   Ganesh Babu, K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Allyl acetate; Allyl alcohol; Allyl chloride

Indexed keywords

ACETIC ACID DERIVATIVE; ACETYL CHLORIDE; ALKENE; ALLYL ALCOHOL; ALLYL COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0142165263     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.063     Document Type: Article

References (35)

1. Caserio F.F., Denis G.E., DeWolfe R.H., Young W.G. J. Am. Chem. Soc. 77:1955;4182.
2. Collington E.W., Meyers A.I. J. Org. Chem. 36:1971;3044.
3. Snyder E.I. J. Org. Chem. 37:1972;1466. Ho P.-T., Davies N. J. Org. Chem. 49:1984;3027.
4. Ho P.-T., Davies N. J. Org. Chem. 49:1984;3027.
5. Corey E.J., Kim C.U., Takeda M. Tetrahedron Lett. 42:1972;4339.
6. Chen K.-M., Joullie M.M. Tetrahedron Lett. 25:1984;393.
7. Munyemana F., Frisque-Hesbain A.-M., Devos A., Ghosez L. Tetrahedron Lett. 30:1989;3077.
8. Lee J.G., Kang K.K. J. Org. Chem. 53:1988;3634.
9. Keramane E.M., Boyer B., Roque J.-P. Tetrahedron. 57:2001;1909.
10. Yadav V.K., Ganesh Babu K., Mittal M. Tetrahedron. 57:2001;7047.
11. (a) Sakurai A., Hayashi T., Hori I., Jindo Y., Oishi T. Synthesis. 1978;370.
12. (b) Boughdady N.M., Chynoweth K.R., Hewitt D.G. Aust. J. Chem. 40:1987;767.
13. Izawa K., Okuyama T., Sakagami T., Fueno T. J. Am. Chem. Soc. 95:1973;6752.
14. Rezgui F., El Gaied M.M. Tetrahedron Lett. 39:1998;5965.
15. Basaviah D., Dharma Rao P., Hyma R.S. Tetrahedron. 52:1996;8001.
16. (a) Hojo M., Sakuragi R., Okabe S., Hosomi A. Chem. Commun. 4:2001;357 (b) Harada T., Akiba E., Oku A. J. Am. Chem. Soc. 105:1983;2771 (c) Nanoshita K., Banno H., Maruoka K., Yamamoto H. J. Am. Chem. Soc. 112:1990;316.
17. (a) Hojo M., Sakuragi R., Okabe S., Hosomi A. Chem. Commun. 4:2001;357 (b) Harada T., Akiba E., Oku A. J. Am. Chem. Soc. 105:1983;2771 (c) Nanoshita K., Banno H., Maruoka K., Yamamoto H. J. Am. Chem. Soc. 112:1990;316.
18. (a) Hojo M., Sakuragi R., Okabe S., Hosomi A. Chem. Commun. 4:2001;357 (b) Harada T., Akiba E., Oku A. J. Am. Chem. Soc. 105:1983;2771 (c) Nanoshita K., Banno H., Maruoka K., Yamamoto H. J. Am. Chem. Soc. 112:1990;316.
19. (a) Gemal A.L., Luche J.L. J. Am. Chem. Soc. 103:1981;5454 (b) Ravikumar K.S., Baskaran S., Chandrasekaran S. J. Org. Chem. 58:1993;5981 (c) Fuller J.C., Stangeland E.L., Goralski C.T., Singaram B. Tetrahedron Lett. 34:1993;257 (d) Nutaitis C.F., Bernardo J.E. J. Org. Chem. 54:1989;5629.
20. (a) Gemal A.L., Luche J.L. J. Am. Chem. Soc. 103:1981;5454 (b) Ravikumar K.S., Baskaran S., Chandrasekaran S. J. Org. Chem. 58:1993;5981 (c) Fuller J.C., Stangeland E.L., Goralski C.T., Singaram B. Tetrahedron Lett. 34:1993;257 (d) Nutaitis C.F., Bernardo J.E. J. Org. Chem. 54:1989;5629.
21. (a) Gemal A.L., Luche J.L. J. Am. Chem. Soc. 103:1981;5454 (b) Ravikumar K.S., Baskaran S., Chandrasekaran S. J. Org. Chem. 58:1993;5981 (c) Fuller J.C., Stangeland E.L., Goralski C.T., Singaram B. Tetrahedron Lett. 34:1993;257 (d) Nutaitis C.F., Bernardo J.E. J. Org. Chem. 54:1989;5629.
22. (a) Gemal A.L., Luche J.L. J. Am. Chem. Soc. 103:1981;5454 (b) Ravikumar K.S., Baskaran S., Chandrasekaran S. J. Org. Chem. 58:1993;5981 (c) Fuller J.C., Stangeland E.L., Goralski C.T., Singaram B. Tetrahedron Lett. 34:1993;257 (d) Nutaitis C.F., Bernardo J.E. J. Org. Chem. 54:1989;5629.
23. Katzenellenbogen J.A., Utawanit T. J. Am. Chem. Soc. 96:1974;6153.
24. (a) Fujii M., Nakamura K., Yasui S., Oka S., Ono A. Bull. Chem. Soc. Jpn. 60:1987;2423 (b) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (c) Kondo K., Tunemoto D. Tetrahedron Lett. 16:1975;1007.
25. (a) Fujii M., Nakamura K., Yasui S., Oka S., Ono A. Bull. Chem. Soc. Jpn. 60:1987;2423 (b) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (c) Kondo K., Tunemoto D. Tetrahedron Lett. 16:1975;1007.
26. (a) Fujii M., Nakamura K., Yasui S., Oka S., Ono A. Bull. Chem. Soc. Jpn. 60:1987;2423 (b) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (c) Kondo K., Tunemoto D. Tetrahedron Lett. 16:1975;1007.
27. (a) Inomata K., Igarashi S., Mohri M., Yamamoto T., Kinoshita H., Kotake H. Chem. Lett. 4:1987;707 (b) Larock R.C., Leung W.Y. J. Org. Chem. 55:1990;6244.
28. (a) Inomata K., Igarashi S., Mohri M., Yamamoto T., Kinoshita H., Kotake H. Chem. Lett. 4:1987;707 (b) Larock R.C., Leung W.Y. J. Org. Chem. 55:1990;6244.
29. Kourouli T., Kefalas P., Ragoussis N., Ragoussis V. J. Org. Chem. 67:2002;4615.
30. (a) Shadakshari U., Nayak S.K. Tetrahedron. 57:2001;4599 (b) Mateus C.R., Almeida W.P., Coelho F. Tetrahedron Lett. 41:2000;2533.
31. (a) Shadakshari U., Nayak S.K. Tetrahedron. 57:2001;4599 (b) Mateus C.R., Almeida W.P., Coelho F. Tetrahedron Lett. 41:2000;2533.
32. (a) Ishizaki M., Niimi Y., Hoshino O. Chem. Lett. 2001;546 (b) Rezgui F., El Gaied M.M. Tetrahedron. 53:1997;15711.
33. (a) Ishizaki M., Niimi Y., Hoshino O. Chem. Lett. 2001;546 (b) Rezgui F., El Gaied M.M. Tetrahedron. 53:1997;15711.
34. Yamaguchi J., Tamada Y., Takeda T. Bull. Chem. Soc. Jpn. 66:1993;607.
35. Julia M., Roy P. Tetrahedron. 42:1986;4991.