Claisen and Intermolecular Rearrangement of Cinnamyloxynaphthalenes

Yutaka Okada, Daisuke Imanari

Department of Applied Chemistry, Ritsumeikan University, Kusatsu-Shi, Japan.

DOI: 10.4236/ijoc.2012.21007                

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.

Keywords

Claisen Rearrangement; Intermolecular Rearrangement; Solvent Effect

Conflicts of Interest

The authors declare no conflicts of interest.

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.