A convenient method for the preparation of aryl cyclopropyl ethers from phenols

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2633-2636

  Hollingworth, Gregory J ^a   Dinnell, Kevin ^a   Dickinson, Laura C ^a   Elliott, Jason M ^a   Kulagowski, Janusz J ^a   Swain, Christopher J ^a   Thomson, Christopher G ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

Alkylation; Cyclopropanes; Ethers; Phenols

Indexed keywords

1 IODO 1 (PHENYLTHIO)CYCLOPROPANE; CARBON TETRACHLORIDE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYL ETHER; METHANOL; PHENOL; PHENOL DERIVATIVE; PHENYL GROUP; PYRIDINOL; SULFIDE; SULFONE; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DEHALOGENATION; METHYLATION; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033605912     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00235-X     Document Type: Article

References (15)

1. Lesher, G. Y. US Patent 4009208.
2. Shostakovskii, S.M., L'vov, A.I., Kimel'fel'd, Ya. M., Izv. Akad. Nauk SSSR, Ser. Khim., 1966, 1754. (CA 66:37558); Retinskii, A.A., Shostakovskii, S.M., Kositsyna, E.I., Izv. Akad. Nauk SSSR, Ser. Khim.1972, 1778 (CA 77:151590); Furukawa, J., Kawabata, N. and Nishimura, A., Tetrahedron, 1968, 24, 53.
3. Shostakovskii, S.M., L'vov, A.I., Kimel'fel'd, Ya. M., Izv. Akad. Nauk SSSR, Ser. Khim., 1966, 1754. (CA 66:37558); Retinskii, A.A., Shostakovskii, S.M., Kositsyna, E.I., Izv. Akad. Nauk SSSR, Ser. Khim.1972, 1778 (CA 77:151590); Furukawa, J., Kawabata, N. and Nishimura, A., Tetrahedron, 1968, 24, 53.
4. Shostakovskii, S.M., L'vov, A.I., Kimel'fel'd, Ya. M., Izv. Akad. Nauk SSSR, Ser. Khim., 1966, 1754. (CA 66:37558); Retinskii, A.A., Shostakovskii, S.M., Kositsyna, E.I., Izv. Akad. Nauk SSSR, Ser. Khim.1972, 1778 (CA 77:151590); Furukawa, J., Kawabata, N. and Nishimura, A., Tetrahedron, 1968, 24, 53.
5. Shostakovskii, S.M., Retinskii, A.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1967, 413. (CA 67:21464); Retinskii, A.A., Tolmasova, V.P., Kotomanova, G.P. and Shostakovskii, S.M., Izv. Akad. Nauk SSSR, Ser.khim., 1968, 164. (CA69:18643).
6. Shostakovskii, S.M., Retinskii, A.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1967, 413. (CA 67:21464); Retinskii, A.A., Tolmasova, V.P., Kotomanova, G.P. and Shostakovskii, S.M., Izv. Akad. Nauk SSSR, Ser.khim., 1968, 164. (CA69:18643).
7. Cimetiere, B. and Julia, M., Synlett, 1991, 271.
8. See Freidrich, B.C. In 'the Chemistry of the Cyclopropyl Group, Part 1' Wiley, Ed. Z. Rappoport 1987, 633.
9. A related strategy utilising an alkoxy stabilising substituent has been reported for the N-cyclopropylation of anilines, see: Kang, J., and Kim, K.S., J. Chem. Soc., Chem. Commun., 1987, 897.
10. Cohen, T. and Matz, J.R., J. Am. Chem. Soc., 1980, 102, 6900.
11. Starting phenols were commercially available except for 4-(triisopropylsilyloxy)phenol which was synthesised by silylation of 4-(benzyloxy)phenol followed by palladium catalysed hydrogenolysis of the benzyl group.
12. Dichloromethane was also found to be a suitable solvent.
13. Prepared according to the procedure of Azuma et al: Azuma.T., Yanagida, S., Sakurai, S., Sasa, S. and Yoshino, K., Synth. Commun., 1982, 137.
14. Greenhalgh, R.P., Synlett, 1992, 235.
15. Trost, B.M., Arndt, H.C., Strege, P.E. and Verhoeven, T.R., Tetrahedron Lett., 1976, 3477.