Loading...
Please wait, while we are loading the content...
Comments on a Conversion of Epoxides to Halohydrins with Elemental Halo- gen Catalyzed by Phenylhydrazine: Tandem Electrophilic Halogenation of Aromatic Compounds and Epoxide Ring Opening to Halohydrins Halogenation of Aromatic Compounds and Epoxide Ring Opening to Halohydrins
| Content Provider | Semantic Scholar |
|---|---|
| Author | Soroka, Sław Goldeman, Waldemar Małysa, Piotr Stochaj, Monika Wrocławska, Politechnika |
| Copyright Year | 2003 |
| Abstract | The ring-opening reaction of epoxides to halohydrins seems to be still a current problem in preparative organic chemistry. Searching in common databases gives more than fifty papers concerning the preparation of 2-halogenoalkanols via ring-opening of epoxides, in the past 15 years. 1 Recently, we found an interesting paper 2 published in this journal, describing a conversion of epoxides to halohydrins with elemental halogens ‘catalyzed by phenylhydrazine.’ The authors proposed a four-step mechanism for this reaction to explain their findings, where the phenylhydrazine plays an essential role as a ‘catalyst.’ Since the authors did not isolate the ‘catalyst’ (unreacted phenylhydrazine) after the reaction from the reaction mixture,3 and because it is unlikely that phenylhydrazine – a very reactive aromatic compound and reducing agent – could survive in the presence of epoxide and in contact with molecular chlorine, bromine, or iodine, we decided to analyse and reinvestigate this reaction. The results of our investigation can be summarized as follows. |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://www.xiuzhengrd.com/ejournals/pdf/synthesis/doi/10.1055/s-2003-42424.pdf |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
