The photoreactions of some diaryl ethers

作者: H.J. Hageman , H.L. Louwerse , W.J. Mijs

DOI: 10.1016/S0040-4020(01)92780-2

关键词:

摘要: Abstract Diphenyl ether,1,4-diphenoxybenzene, and some substituted diaryl ethers have been irradiated in solution. The reactions observed are: (1) cleavage of the ether bond(s) followed by H-abstraction from solvent yielding phenols benzene derivatives, (2) a photo-Claisen type rearrangement 2- and/or 4-hydroxybiphenyl derivatives. product distribution was found to depend on solvent. o/p ratio diphenyl be concentration dependent, o-isomer increasing at expense p-isomer dilution.

参考文章(10)
M. S. KHARASCH, G. STAMPA, W. NUDENBERG, Photochemical para Rearrangement of Phenyl Ethers. Science. ,vol. 116, pp. 309- 309 ,(1952) , 10.1126/SCIENCE.116.3012.309
L. Schutte, E. Havinga, Investigations into a possible14C isotope effect in photodissociations Tetrahedron. ,vol. 23, pp. 2281- 2284 ,(1967) , 10.1016/0040-4020(67)80063-2
B. H. Bibo, H. L. Louwerse, Analysis of 2,6-substituted cyclohexanones and phenols by gas-chromatography combined with thin-layer chromatography Fresenius Journal of Analytical Chemistry. ,vol. 236, pp. 208- 215 ,(1968) , 10.1007/BF00503275
L. D. Metcalfe, Ross J. Martin, Technique for coating gas-liquid chromatography capillary columns using long chain quaternary ammonium compounds Analytical Chemistry. ,vol. 39, pp. 1204- 1205 ,(1967) , 10.1021/AC60254A006
H.-I. Joschek, Sidney I. Miller, Photocleavage of phenoxyphenols and bromophenols. Journal of the American Chemical Society. ,vol. 88, pp. 3269- 3272 ,(1966) , 10.1021/JA00966A018
J. F. Klebe, H. Finkbeiner, D. M. White, Silylations with Bis(trimethylsilyl)acetamide, a Highly Reactive Silyl Donor Journal of the American Chemical Society. ,vol. 88, pp. 3390- 3395 ,(1966) , 10.1021/JA00966A038
THOMAS C. BRUICE, NORMAN. KHARASCH, RICHARD J. WINZLER, THE SYNTHESIS OF SOME NEW THYROXINE ANALOGS Journal of Organic Chemistry. ,vol. 18, pp. 83- 91 ,(1953) , 10.1021/JO01129A014
Michael R. Sandner, David J. Trecker, Mechanism of the photo-Fires reaction Journal of the American Chemical Society. ,vol. 89, pp. 5725- 5726 ,(1967) , 10.1021/JA00998A053
D.P. Kelly, J.T. Pinhey, R.D.G. Rigby, The photochemical rearrangement of aryl ethers Tetrahedron Letters. ,vol. 7, pp. 5953- 5956 ,(1966) , 10.1016/S0040-4039(01)84151-4
H. Stegemeyer, Photochemische Bildung fünfgliedriger Ringsysteme Naturwissenschaften. ,vol. 53, pp. 582- 583 ,(1966) , 10.1007/BF00600533