Zeolite beta Induced Rearrangement of Allyl Benzyl Ethers. 6. Variation of the Aromatic Part and Synthesis of Dihydronaphthalene Derivatives.
The zeolite beta induced rearrangement of substituted allyl benzyl ethers to give 4-arylbutanals was investigated with respect to the substituents in the aromatic ring. In some cases the resulting aldehydes cyclized spontaneously to give dihydronaphthalene derivatives. The rearrangement and also the ring closure to dihydronaphthalenes failed or gave poor yields in cases where too weak electron-donating substituents were present in the aromatic ring. Also the dimensions of the pore size of the zeolite in relation to the transition state of the cyclization seemed to be of importance. Replacement of the benzylic part with other structures potentially capable of stabilizing cationic centers have hitherto not resulted in successful rearrangements.
Wennerberg
Johan
J
Organic Chemistry 1, Department of Chemistry, Lund University, P.O. Box 124, S-221 00 Lund, Sweden.
Ek
Fredrik
F
Hansson
Anna
A
Frejd
Torbjörn
T