Direct oxidative conversion of alkyl halides into nitriles with molecular iodine and 1,3-diiodo-5,5-dimethylhydantoin in aq ammonia

Various benzylic halides were smoothly and directly converted into the corresponding aromatic nitrites in high yields using molecular iodine and 1,3-diiodo-5,5-dimethylhydantoin, respectively, in aq ammonia. Similarly, primary alkyl halides were also converted into corresponding nitrites in moderate to good yields using molecular iodine and 1,3-diiodo-5,5-dimethylhydantoin in aq ammonia, although a long reaction time was required. The present reaction is a new method for the preparation of aromatic nitrites from benzylic halides and a new method for the conversion of alkyl halides into corresponding nitrites with retention of the number of carbon atoms. (C) 2009 Elsevier Ltd. All rights reserved.