ChemInform Abstract: Regioselectivity of the Amino-Claisen Rearrangement. The Rearrangements of N-Allyl-9-methoxy-1-oxajulolidinium Bromide and N-Allyl-8-methoxylilolidinium Bromide.
Abstract
Thermolysis of N-allyl-9-methoxy-1-oxajulolidinium bromide (I) and N-allyl-8-methoxylilolidinium bromide (III) gives the meta-rearranged products (IIa) and (IVa) respectively, accompanied by the deallylation products (IIb) and (IVb) respectively.
ChemInform Abstract
Thermolysis of N-allyl-9-methoxy-1-oxajulolidinium bromide (I) and N-allyl-8-methoxylilolidinium bromide (III) gives the meta-rearranged products (IIa) and (IVa) respectively, accompanied by the deallylation products (IIb) and (IVb) respectively. In the presence of sodium hydrogen carbonate para-rearrangement occurs with (III) to give the allyl compounds (V) and (VI) as the main components. NaHCO3has only little effect on the thermolysis of (I), giving (IIa) and (IIb) in 95% and 4% yield respectively. (MS-, IR-, 1H-NMR-data).