IJOC  Vol.2 No.1 , March 2012
Claisen and Intermolecular Rearrangement of Cinnamyloxynaphthalenes
ABSTRACT
Rearrangements of the 1- and 2-cinnamyloxynaphthalenes undergo in diethylene glycol and decalin with solvent de-pendence. In 2-cinnamyloxynaphthalene, the Claisen rearrangement occurs regardless of the solvents. However, for the 1-analogue, the Claisen rearrangement occurs in decalin, while both the Claisen and intermolecular rearrangements occur at higher temperatures in diethylene glycol.

Cite this paper
Y. Okada and D. Imanari, "Claisen and Intermolecular Rearrangement of Cinnamyloxynaphthalenes," International Journal of Organic Chemistry, Vol. 2 No. 1, 2012, pp. 38-43. doi: 10.4236/ijoc.2012.21007.
References
[1]   L. Claisen, “Rearrangement of Phenyl Allyl Ethers in C-Allylphenols,” Berichte der Deutschen Chemischen Gesellschaft, Vol. 45, 1912, pp. 3157-3166. doi:10.1002/cber.19120450348

[2]   C. D. Hurd and M. A. Pollack, “Mechanisms for the Rearrangements of Ethers: γ-Ethylallyl Phenyl Ether and γ-Ethylallyl Vinyl Ether,” Journal of Organic Chemistry, Vol. 3, No. 6, 1939, pp. 550-569. doi:10.1021/jo01223a004

[3]   E. N. Marvell, B. J. Burreson and T. Crandall, “Influence of Alkyl Groups on the Rate of the Para Claisen Rearrangement,” Journal of Organic Chemistry, Vol. 30, No. 4, 1965, pp. 1030-1032. doi:10.1021/jo01015a018

[4]   D. Y. Curtin and H. W. Johnson Jr., “Mechanism of the para Claisen Rearrangement. Evidence for a Die-none-Phenyl Ether Rearrangement,” Journal of the American Chemical Society, Vol. 78, No. 11, 1956, pp. 2611- 2615. doi:10.1021/ja01592a078

[5]   Y. Okada, M. Adachi and T. Hayashi, “Substituent Effect on Claisen Rearrangement of 1-Substituted 2-Cinnamy- loxybenzenes,” Journal of Oleo Science, Vol. 51, No. 5, 2002, pp. 359-364. doi:10.5650/jos.51.359

[6]   T. Hayashi, Y. Okada, K. Arita and H. Kuromizu, “Solvent Effect on the Thermal Rearrangement of Cinna- myloxybenzene,” Nippon Kagaku Kaishi, No. 4, 1997, pp. 255-259. doi:10.1246/nikkashi.1997.255

[7]   H. Schmid and K. Schmid, “The Claisen Rearrangement. I. Experiments with Carbon 14. 2,” Helvetica Chimica Acta, Vol. 35, 1952, pp. 1879-1890. doi:10.1002/hlca.19520350612

[8]   H. Schmid and K. Schmid, “The Claisen Rearrangement. II. Experiments with Carbon 14. 3,” Helvetica Chimica Acta, Vol. 36, 1952, pp. 489-500. doi:10.1002/hlca.19530360218

[9]   T. Hayashi, Y. Okada and T. Inaba, “ Catalytic Effect of Metal Salts on the Claisen Rearrangement of 1- and 2-(Allyloxy)naphthalene and 8-(Allyloxy)quinoline,” Chemistry Express, Vol. 51, 1997, pp. 255-259.

[10]   J. Tsai, S. Li Chen, L. Chen, P. Chen, S. Hsu, C. Lin and E. Wang, “Synthesis of Substituted 2,5-Dihydro-1- naphthoxepines from 1-Naphthol via Ring-Closing Metathesis,” Arkivoc, 2008, pp. 205-217.

 
 
Top