Abstract
In a converting reaction of $p-bromo-\alpha-diethylaminoacetophenone$ (1a) and $p-bromo-\alpha-piperidinoacetophenone$ (1b) with KCN and $(NH_4)_2CO_3$, to hydantoin, the expected 5-(p-bromophenyl)-5-diethylaminomethylhydantion (2a) and 5-(p-bromophenyl)-5-piperidinomethylhydantoin (2b) were not formed. Diethylaminomethyl group and piperidinomethyl group were eliminated and p,p'-dibromodiphenylhydantil (4), which might be formed through dimerization of 5-(bromophenyl)-hydantoin (3), and p-bromobenzoic acid (5), which was formed through a degradation of 5-(bromophenyl)-hydantoin, were obtained. In the case of $p-bromo-\alpha-morpholinoacetophenone$ (1c), the expected 5-(p-bromophenyl)-5-morpholinomethylhydantoin (2c) was formed.
파라-브로모-알파-디에틸아미노아세토훼논(1a)과 파라 브로모-알파-피페리디노아세토훼논(1b)의 Bucherer-Bergs 히단토인 형성반응에 있어서 예상되는 화합물인 5-피페리디노메틸히단토인(2b)이 형성되지 않았다. 디에틸아미노메틸기와 피페리디노메틸기가 이탈되고 5-(파라-브로모훼닐)히단토인 (3)의 이합체화반응으로 형성된 것으로 볼 수 있는 p,p'-디브로로디훼닐히단틸(4)과 5-(파라-브로모훼닐)히단토인의 분해산물로 생각되는 파라-브로모벤조산(5)이 형성되었다. 파라-브로모-알파-몰포리노아세토훼논(1c)의 경우에 있어서는 예상화합물인 5-(파라-브로모훼닐)-5-몰포리노메틸히단토인(2c)이 형성되었다