
TY  - JOUR
A1  - Mooney, BA 
A1  - Prager, RH 
A1  - Ward, AD 
T1  - Central nervous system active compounds. V. Claisen rearrangement products of allyl vinyl ethers obtained from caprolactam derivatives
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 12
SP  - 2717
EP  - 2728
KW  - 
UR  - https://doi.org/10.1071/CH9802717 
N2  - A series of allyloxy unsaturated tetrahydroazepinones has been prepared and their Claisen rearrangements have been investigated. The 4-allyloxy compounds (4a-e) rearranged thermally to give the 3-substituted hexahydro derivatives (9). In some cases further reaction products were obtained, particularly when higher temperatures were used. Rearrangement of the 4-propargyloxy system (4f) proved more complicated, and N-allyl-2,3,4,5-tetrahydro-1H-azepin-2-one derivatives (21a,b) were unreactive. Alkylation of the hexahydroazepine-2,4-dione system (3) with various allyl halides gave mixtures of the 3-mono-(20) and the 3,3-di-substituted (19) products. The unsaturated ethers generally showed marked muscular depression on the central nervous system of mice, while their rearrangement products were only weakly depressant. 
ER  -

