Abstract
It was found that 4- (N-allyl-N-tosylamino) naphthal-N-methylimide (2) rearranged to 3-allyl-4-tosylamino derivative (3) by a first-order mechanism. When heated at 230°C for 1 2/3 hours under a reduced pressure, (2) was converted into (3) in 74.5% yield, but further heating brought the decomposition of the reaction mixture. The decomposition was attributed to the presence of atmospheric oxygen. The rate constant of the rearrangement is 7.6×10-5 sec-1 (213.1°C) by no use of solvent and 6.1×10-5 sec-1 (213.0°C) in N, N-diethylaniline.
The structure of (3) was confirmed by covnerting it to 3-propenyl-4-tosylamino derivative (4) (which was also obtained from the known 3-allyl- (5) and 3-propenyl-4-methoxy derivative (6) respectively) and further, to the cyclization product (7) by bromine.
The sulfuric acid-hydrolysis of (2) and (3) was attempted.
