A new, simple procedure for the generation and addition of HI to alkenes and alkynes using Bl3:N,N-diethylaniline complex and acetic acid
✍ Scribed by Ch. Kishan Reddy; M. Periasamy
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 109 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Hydroiodic acid generated in situ from Bl3:N,N-diethylaniline complex and acetic acid~ readily adds to alkenes and alkynes in Markovnikov fashion to form alkyl and alkenyl iodides in good yields under mild conditions.
Markovnikov addition of hydrogen halides to alkenes and alkynes is one of the most important reactions in organic chemistry. Classically~ this reaction is carried out with gaseous hydrogen halides. I However~ there is still interest on the development of more convenient procedures for this reaction. For example, recently it has been reported that the reaction can be more advantageously accomplished by stirring at tlS°C a heterogenous mixture of alkene (l mol)~ hexadecyltributylphosphonium bromide (0.1 mole) and aqueous hydrohalogenic acid 2 (3-1~ mole). More recently, it has been reported that HI addition to some alkenes and l-hexyne can be achieved using activated A1203-I 2 in refluxing petroleum ether. 3 We wish to report that the HI addition to alkene and alkyne can be achieved under relatively mild condlticns using Bl3:N,N-diethylaniline ~ generated using 12~NaBH 4 and the amine in the presence of acetic acid. 4-6